It was 2001; and my boss was impressive — some would say intimidating. A whiz-kid founder and CEO of a fast-growing start-up that had raised capital at lofty valuations, he was precociously business-savvy and had a seemingly unshakable self-confidence. All of which made it that much more remarkable when he put his hands up and uttered those unforgettable words: “You convinced me.”

The truth is that we had very different leadership styles; and I often found myself filing the minority report when it came to debates among our company’s leadership team. But on this day, (and many times thereafter), I was grateful to be offered the opportunity to successfully make my case. I remember being surprised that day about the outcome itself, and about the impact it had on me — I’ll never forget that feeling of having a real voice in the business. Fast forward twenty years: I participate in many similar business debates, but now I often find myself in the senior role. I’ve learned that those same three words have enormous power, not only to make someone’s day…but to profoundly influence how businesses tackle challenges. I try to keep them top of mind and use them whenever possible. Below are some thoughts on why this practice works so well and some safety precautions when wielding this powerful tool.

At a primal level, it’s obvious why this can be such a potent approach — it is a succinct and unambiguous way for leaders to share decision-making authority with less senior folks. Beyond that, though, some subtle nuances make it consistently effective in small-scale growth companies:

Like any powerful instrument, though, using this approach comes with related dangers. Below are a few cautionary thoughts for the safe operation of this tool.

Looking back, I realize how much I learned from that boss back in the early 00’s; and no lesson was more valuable than this one. Having a legitimate forum to change our CEO’s thinking offered a feeling of empowerment that I still haven’t forgotten. And, I was a member of the senior leadership team…which further highlights just how impactful it can be when leaders create this type of environment all throughout their organizations. A big step in this direction can be taken with three simple words: “You convinced me.”

From time to time, we use this forum to share observations and trends from webinars or virtual conferences (here); and sometimes we invite guest-bloggers to offer insights from their own experiences (here and here). This post does both of those things at once. Our friend and peer, Mike Dzik, is a Growth Partner at Radian Capital (full disclosure: one of Lock 8’s investors), where he works with Radian’s portfolio companies on their respective go to market strategies spanning marketing, sales and customer success initiatives. Last week, Mike attended the TOPO Virtual Summit a three-day virtual conference for sales, sales development, and marketing practitioners; and he was generous to share with us his impressions of the event. He’s also agreed to allow us to share those observations here on Made not Found. So, with no further ado, I’ll turn it over to Mike, below:

I hope everyone is doing well and off to a fast start for Q4. I spent some time attending the TOPO Virtual Go To Market Summit this week and wanted to share 5 key themes surrounding 2021 (below).

  1. Painkillers over Vitamins: Buyers are looking for faster impact. 90% of enterprise buyers are focusing on tactical results and improvements within the first 90 days after purchase. While many sales have evaporated during COVID, the deals that are getting done are being done inside shorter sales cycles (Days to Close (DTC) is dropping) as contract values are expanding (Average Contract Values (ACV’s) are rising). Takeaway: Now more than ever, focus on the “painkillers” in your pitch, not the “vitamins”.
  2. Speed Wins: Speed and agility on your GTM motion are now the two biggest keys to success. Speed with regard to changes in marketing message, deck/demo, pricing and anything else that helps you out-maneuver bigger/more entrenched competitors is essential during times of stress and uncertainty. Takeaway: Don’t fall in love with your message; rather, try new approaches and refine them in the context of a rapidly changing market landscape.
  3. Double Down on Community: In times of crisis, people turn to trusted business contacts and ask them for recommendations on how to solve problems. Word of Mouth (WOM) is a huge catalyst to buying decisions right now. If you have a large user community, figure out how to cultivate it more than ever. If you don’t currently have an active community base, think about taking steps to start building it now. Takeaway: Activate your community — even more than usual — as a highly credible component of your market message.
  4. Get your “Revenue Operations” Program Straight: You need to unify your data, systems and process across your GTM motion for maximum clarity and understanding. This is a more complex effort than just having a Sales Ops function and it can be hard / expensive to implement. Takeaway: In spite of the high effort required, Revenue Operations yields greater visibility into the business for faster decision making, which is critical in the current business climate.
  5. Sales Enablement is Key: Sales Enablement is a relatively new term, but it is fast becoming key to growth. You need to adapt and change your GTM motion quickly in this turbulent period and having sales enablement dialed-in can help you with new plays, new case studies, new collateral and messaging. The AE to Sales Enablement ratio has gone from 30:1 in 2017 to 20:1 in 2020 showing how companies are investing more, not less, even in a downturn. Takeaway: investing in enabling the success of revenue generators is worthwhile, even when making such investments can be hard to justify.

Thanks, Mike, for these pearls. There are so many good virtual events out there; and it is impossible to free up the space to attend them all. We’re grateful to benefit from your participation in, and distillation of, the thought leadership coming out of the TOPO Virtual Summit.

-Todd

The television series Undercover Boss has been a guilty pleasure of mine for years. Now entering its eleventh season, the show features “high-level corporate execs (who) leave the comfort of their offices and secretly take low-level jobs within their companies to find out how things really work and what their employees truly think of them.” For cringe-worthy viewing, this one totally hits home for me.

But I also like the show’s more serious theme of “walking a mile in someone else’s shoes” in order to deeply understand that person’s experience. At Lock 8, we’ve adapted this concept to help provide insight into a key focus area for small-scale SaaS businesses. Whereas Undercover Boss leverages this approach to offer candid employee-level views into the internal workings of companies, we hope to shine a light on the experience a customer has when evaluating, selecting, and adopting a B2B software solution.

On the surface, this is a straightforward endeavor, involving a few simple steps:

  1. Pretend you are a prospect or potential customer of your company’s product
  2. Go through the steps of buying / implementing / using that product
  3. Record your experiences (good, bad, and ugly) throughout that process
  4. Articulate what would be the absolute ideal experience for what you just went through
  5. Identify the gaps between #3 and #4 above; build a plan to eliminate those gaps

Simple enough, right? Not really. Like so many things, this is easy to do poorly, and extremely difficult to do well. To help make it easier, this post will share a few tips relating to each of these deceptively challenging steps.

1. Pretend You Are a Prospect: At its most basic level, this is a role-playing exercise, so it’s absolutely critical to play your role well. This may be relatively easy for the undercover bosses referenced above (they get a cover legend and a disguise; and they go), but it is more complicated to get inside the mind(s) of a purchasing committee for a large and complex corporate enterprise. We’ve learned that it is definitely worth investing the time and effort to make it real: have a dossier, real personas, real business problems you’re solving for, deadlines, budget constraints, and even political motivations. Even go so far as to designate a few people to play different decision-maker roles. Balance the company profiles to reflect your current (vertical) targets, your buyer personas spectrum and the maturity of organization using your solution. Marketing absolutely should help develop these resources. Here’s a snapshot of just part of a dossier created by a portfolio company that recently executed such an initiative.

An additional point about this step: BE OPEN! Unlike the undercover bosses, for whom secrecy is paramount, this should NOT be a clandestine endeavor. The reality in software companies is that everyone somehow touches the customer experience. Likewise, our experience is that people in early-stage SaaS business are all operating in good faith, so there is no need to trick anyone or attempt to trip them up. Rather, everyone needs to know you’re undertaking such a journey; and each functional area needs to be part of the process. Now…you may need to make the case: why it’s important; why we need to get it right; who’s involved; what we’ll be doing; how we’ll share feedback. But these are all further arguments for doing this out in the open. Equally important: everyone at the company should hear later what was discovered, and to view the information as a learning opportunity, not a judgement. Nothing makes people more nervous than being excluded from understanding what’s happening behind the scenes or feeling like this is a test.

2. Go Through the Steps: Uh…what steps? Whereas most businesses have established a sales process with related stages and activities, these usually assume a company-centric approach, and overwhelmingly ignore the customer perspective. Customers’ motivations / activities / dynamics are effectively infinite, so identifying their purchasing steps can be paralyzingly complex. To simplify, we like to organize our efforts around “major stages” of the customer’s lifespan with a software solution. Although every product / system / technology is unique, there is a relatively small number of macro-phases on the customer journey; and these are generally consistent across different solutions. The purpose of the mental model and accompanying graphic below is to align perspectives, offer a shared vocabulary, and provide structure to the exercise.

On the principle that a picture is worth a thousand words, I’ll hope this graphic is self-explanatory. In summary, as we engage in countless customer “buying” and “owning” activities, and we organize them into these six phases: (1) awareness, (2) evaluation, (3) decision, (4) on-boarding, (5) use, and (6) advocacy. One note of caution: for complex solutions, this may end up being a grueling multi-month process. It’s important to know what you are signing up for in advance…and what your customers are going through to buy / use your products.

3. Record Your Experiences: A disciplined collection of notes will generate consistency of insight and evaluation. With more than one person involved the experience, it’s important to provide a consistent way to gather intel and feedback. That said, this doesn’t require over-thinking; and a simple note template suffices. We like an “Experience and Expectation” framework (“what did I expect?” and “what did I experience?”) to structure things. Then, just codify the experience in a linear way — capture in detail and in chronological order what happened and how it impacted the buying / owning processes outlined above.

4. Articulate the Ideal: It’s nearly impossible to simply dream up the ideal client experience, just like it is unheard of to nail product-market-fit on version 1.0 of a solution. Instead, it pays to inspect and adapt. Thankfully, the early steps of this exercise, and the current-state baseline they provide, offer an awesome foundation from which to iterate toward a vastly enhanced client experience. As a result, this step can be as simple as revisiting every step along the journey and answering the following question: “what would have made this much better?” In the best case, this can lead to a wholesale re-thinking of the journey; at a minimum, it will radically improve the existing steps of the experience.

5. Identify gaps; build a plan: For the activators in the crowd, this is the payoff where you can begin to implement necessary improvements. But be careful about succumbing to temptation. It is alluring to focus energy on an ad hoc basis to address the low hanging fruit that can be fixed easily. The problem is that this approach can break any number of existing processes that — although they may be sub-optimal — generally work today in the context of the current approach. So be careful about what you choose to “fix” as a one-off — it could just break other areas of your process. Although it requires more patience and offers delayed gratification, an orchestrated program overhaul will undoubtedly yield more substantive improvement of the overall client experience. Make a plan and take your time in executing it. Our experience is that the “customer experience re-engineering” project to come out of this exercise may take months or even years to implement.

As with most pressing, cross-company business issues, initiatives like creating an awesome CX Journey can take on a life of their own. Proceed with caution here; ensure that anything and everything you chose to do ties back to your overarching business needs. Such an effort must involve more than just the bosses; and there is no need to go undercover — doing so will allow companies to walk in their customers’ shoes…a journey well worth taking.

As a card-carrying introvert, I’ve always found industry conferences to be exhausting. Likewise, over recent months, Zoom Fatigue consistently crushes me by mid-day Friday. So, I figured that a pandemic-induced remote conference would be some kind of “snakes on a plane” hybrid, uniquely designed for my personal torture. But, having just concluded my first honest-to-goodness attendance of a multi-day virtual trade conference, I am pleased to report that I was totally wrong. Rather, the SaaStr Annual at Home conference this week was engaging, informative, and — I can’t believe I’m writing this — energizing. Having been freed from the relentless distractions and demands of in-person conferences (networking, generating leads, striving to optimize investment in Travel & Entertainment), I paid much closer attention to the valuable content sessions than I normally would. I also appreciated moments of respite throughout the day which offered the opportunity to sense-make across sessions. The net result was a solid set of takeaways for a fraction the time / effort (and $); and I thought I’d share an eclectic mix of conference tidbits below.

1. “ARR is a fact, churn is an opinion:” This was a gem from one of my favorite sessions led by Dave Kellogg, who offered a fast-paced “how-to” of useful SaaS metrics. The specific point here is that churn can be defined and manipulated in many ways (true!), with collateral damage to the integrity of other metrics (also true). The broader point, which he supported with compelling data — focus on what matters to value-creation in the business. Roger that. (Session: “Churn is Dead. Long live Net Dollar Retention with Dave Kellogg”).

2. Remaining Performance Obligation (RPO) Intro: As a quick-and-dirty definition, RPO can be thought of as deferred revenue plus backlog. The Motley Fool offers a deeper explanation here, in connection to Splunk. This item came from the same “Churn is dead” session, which was the first time I’ve heard RPO referenced in connection to private companies. Makes total sense, and I’m eager to think about this more in the context of usage-based business models. (Session: “Churn is dead. Long live Net Dollar Retention Rate with Dave Kellogg”).

3. Managing Complex ChangeArquay Harris of Slack led one of my favorite sessions, and not just because she threw out the term Kobayashi Maru in her talk (her content was valuable and preso style was super-engaging). She referenced Sylvia Duckworth (the introduction to whose work alone was worth the price of admission) and shared the deceptively powerful graphic below which captures elements of managing complex change.

I’ve written here about principles of leading change, but I think this graphic captures these concepts in an amazingly clear, concise, and digestible way. There is a 100% chance I’ll be re-using this visual down the line. (Session: “The Secrets of Managing in All Directions with Slack”).

4. Committee Buying: It’s not our imagination, there is much more buying-by-committee mid-pandemic among enterprises who are increasingly risk-averse, cost-conscious, and looking to consolidate their technology investments. Lots of work to be done around understanding more / new buyer personas and how to sell into a flatter organization where any single person has veto power. (Session: “Buying Patterns in the Enterprise: Who’s Really Buying & Why in a Post-Covid World with G2”)

5. Privacy Debt: Bessemer Venture Partners shared six predictions around the 2020 State of the Cloud (janky photo below):

Why Can’t I Get PrScr to Work When I Need It?

The one that really resonated with me was: “Privacy debt will be the new tech debt.” In short, SaaS players that have not been making consistent, diligent investment in their solutions’ privacy envelope will undoubtedly face a reckoning where significant, costly catch-up on this front will be unavoidable. I suspect tech debt will continue to be a problem for many companies, so I’d maybe argue that privacy debt is yet another straw on the camel named “Tech Debt.” (Session: “State of the Cloud 2020: The COVID Beneficiaries Edition with Bessemer Venture Partners”).

6. Fun Still MattersBen Chestnut, founder and CEO of marketing platform giant Mailchimp, shared a great story of the moment when his development team transitioned from being mercenaries (less-productive clock-watchers) to missionaries (self-motivated true believers). It was when they started programming Easter Eggs into the solution. The point? Having fun is incredibly powerful in terms of culture, talent retention, brand, and so much more. True that — awesome interview. (Session: “Learning from the Lows: How Mailchimp Navigated Economic Uncertainty”).

7. Vertical SaaS Rules (Part 1): There were a number of sessions that focused on issues relating to vertical-specific SaaS businesses. We are big fans of vertical SaaS at Lock 8, so I enjoyed these immensely. Damola Ogundipe talked about how being a vertical SaaS solution gives Civic Eagle a leg-up in recruiting because it is easier to identify for culture and passion (and not just talent) relative to horizontal players. (Session: “Underserved Markets for SaaS Companies with Backstage Capital, Avisare, and Civic Eagle”).

8. Vertical SaaS Rules (Part 2)Songe Laron, CEO and Co-Founder of Squire made a compelling argument for why vertical SaaS solutions have an inherent advantage over their horizontal peers in terms of increasing average revenue per unit (ARPU) within their focused customer base. That same session underscored the corresponding point that market sizes for vertical SaaS players were often a whole lot bigger than they first appear…and that domain expertise in that market enables savvy operators to unlock TAM that remains hidden to the casual observer. Exactly! (Session: “Vertical SaaS 2.0: How Barbershops Are Creating a SaaS Rocketship with CRV and Squire”).

9. D&I — Early but Mighty: The topic of diversity and inclusion was understated, but never far from center-stage at this conference; and it came up in various organic ways throughout many sessions. I also attended one session where it was the explicit focus (“Which D&I Initiatives Really Work: The metrics you should be tracking with Notion Capital”). That session crystallized a shared conviction that advancing D&I in SaaS businesses is not only the right thing to do, but that it is also highly correlated with value creation…even as we are still early-on in the collection of supporting empirical evidence. In sum, I sensed that (a) this will be a major focus for SaaS businesses that acknowledge there is much to be done, (b) there is early demonstrable progress being made, (c) it doesn’t appear that anyone has all the answers, and / but we are feeling our way together.

10. “On” and “In the Business” versus “Out”: There is a well-known distinction between “working on your business” versus “working in your business.” What I have sometimes found off-putting about software conferences is the seemingly obsessive focus on “working out of your business.” By that I mean placing overwhelming emphasis on exits, liquidity, and valuation. Don’t get me wrong, those things are extremely important; but they can also suck all the oxygen out of the room. In this crazy, tragic COVID reality we are living through, I found that NOT to be the case at this event. Rather, I found that people were very much focused on “working on their businesses;” and it was really refreshing.

And…1 to Grow On (Humble Pie is Comfort Food): Similar to the point above, there can be a lot of posturing that occurs at SaaS conferences, and this tends to escalate in direct correlation with SaaS company valuations. Although SaaS multiples remain durable, the past six months have been enough to inject a bit of humility into all of us. This seemed evident in most sessions, where I perceived a genuine air of people wanting to support one another and offer humble assistance where possible. It created a comfortable environment for a conference; I certainly hope this aspect of our current environment has some staying power.

It is a good thing to be “coachable,” meaning capable of being easily taught and trained to do something better. It’s easy to understand why companies consistently seek to hire and reward coachable behavior in their teams. Based on this definition, I’d argue we all want to be coachable. Unfortunately, our egos often get in the way. This likely explains the countless books and articles that provide tips on how to become more coachable. These serve a valuable purpose; and I don’t have a beef with any of them. With one exception: their guidance seems to overwhelmingly focus on junior level professionals, and to largely ignore senior executives. At Lock 8, we strongly believe in the power of coaching to elevate the performance of executives and (correspondingly) the businesses they lead. This post shares some experiences and observations around coaching / coachability for people who need it just as much as anyone — seasoned senior leaders of small-scale businesses.

Contrary to popular belief, the need for coaching does not decrease as one’s proficiency / expertise / seniority increases. Elite performers of all types (e.g. athletes, performing artists, authors, painters, etc.) all tend to utilize more coaching, not less, as they advance in their respective fields. Want evidence: have you noticed the sideline of a big-time football game in recent years?

And yet, an anecdotal sampling of articles about coachability in the workplace shows an overwhelming focus on the most basic aspects of the topic. One recent article from a highly respected publication offered five tips for being more coachable — and all five of them focused on responding well to feedback. Although requesting / receiving feedback is an undeniably valuable skill, I’d argue it is a necessary, but insufficient condition to being coachable. For executives aspiring to become more coachable as their careers progress, simply getting better about asking for feedback won’t move the needle.

This all has been top-of-mind for me lately: I recently resumed working with an executive coach, after a six-year hiatus from doing so on a formal and consistent basis. The experience has been really positive. And it has been a reminder that there are wide variations in these coaching sessions, with some being truly groundbreaking and others not so much. Reflecting on this, I’ve realized that the variations are largely of my own making. Certain behaviors elevate the results, while others undermine my efforts to be coached. In short, the outcome depends on how “coachable” I’ve been in connection to a particular session. Below are some observations around my recent exec coaching experience, in hopes that they will help other execs who are looking to optimize their own coachability.

  1. Nike Rule: Just Do It. Seriously, a huge step toward execs becoming more coachable is making the commitment to formally work with an executive coach. This seems obvious, but it’s surprisingly hard. First, there is a lot of inertia against taking the plunge. Second, it can be expensive. Third, I personally have found it consistently challenging to find a coach I actually WANTED to work with (perhaps more on that in a future post). Finally, we tend to convince ourselves that receiving regular (or even irregular) feedback from various colleagues / employees / peers / board members is tantamount to coaching. It’s not –it’s just varyingly structured feedback that should be absorbed and internalized, but also viewed through whatever prism it’s being delivered. Conversely, establishing a formal exec coaching relationship (and paying for it), immediately fosters a coachable mindset in the person being coached.
  2. Embrace vulnerability: Leaders generally are relied upon to provide guidance and strength to others. And while we’ve largely / thankfully outlived taboos against company leaders showing weakness, a complex dynamic exists for them across the concepts of vulnerability, safety, and competence (I made a quick video on this topic here). The result is that there are precious few situations where leaders can fully display vulnerability. Coaching sessions are that place. Let it all out — personal doubts, fears about the business, nagging weaknesses — they are all open topics, with no negative repercussions for raising them. If naming a problem is a first step toward solving it, then these sessions are the safest place to take that all-important first stride. Run to it.
  3. Be Prepared: Aside from being one of my favorite musical numbers from The Lion King (1994), “Be Prepared” has become my new motto for these coaching sessions. It strikes me that there is a near-linear correlation between time spent on active preparation in advance of a coaching session, and the productivity of the session itself. My best results roughly reflect a 1:1 ratio (60 minutes of prep per 60-minute session). This generally falls into two buckets: (a) writing down thoughts as follow-up to topics / exercises that arose in the prior session and (b) codifying (and sharing with my coach in advance) a set of themes that I’d like to explore in the upcoming session. This allows my coach to optimize our time together and dig-in with real focus, while still leaving room for unscripted exploration. The less I prepare, the more I devolve into free-association without purpose — which strikes me as being in direct conflict with the definition of coachability above.
  4. Talk More, Smile Less: With all due respect to Aaron Burr in Hamilton (“Talk less, smile more”), being coachable demands unapologetically open and honest voicing of one’s positions and beliefs. This runs counter not only to Burr’s advice, but also to what we are encouraged to do from a young age (“We have two ears and one mouth for a reason…). But talking things out is a necessary component of being coachable, especially for external processers like me. This guideline applies not just to our fears / concerns (per the vulnerability point above), but also to our hopes and dreams. Brazenly expressing our most ambitious goals, irrespective of how insanely audacious they may be, will spur a constructive discussion about the current realities, options available, and execution required to achieve them.
  5. Ask to be Asked: As thoughtful coaches will assert, their role is not to dispense advice or impart gems of wisdom, but rather to ask provocative questions. This point is especially true in the context of coachable executives, since we don’t typically do this for ourselves. Left to our own devices, business leaders are adept at coming up with answers / solutions — it’s what we do. But we are less good at asking and holding ourselves accountable to answering deep questions. We are just too ____________ (pick one: busy / invested / scared / lazy / committed to the current path(?)) to do it consistently. That’s what executives should ask coaches to do for them. The less I expect my coach to tell me stuff, the more I empower her to ask tough questions, the better our results are. As a related aside, this point should help debunk the common misconception that a coach needs to be more expert at a given pursuit than the person receiving the coaching. Wrong. If this were true, how would Beyonce or Roger Federer or Simone Biles select a coach? Spoiler: They all have coaches whose role is to help these G.O.A.T.s challenge themselves.
  6. Read, read, read: I find that my coachability rises on weeks when I’ve read a wide range of business-related books / blogs / articles. This one might also seem obvious; reading undeniably expands our knowledge base, which naturally improves our ability to learn. But I include it here for what might be an unexpected reason: Reading about the business challenges and successes of others reinforces just how unremarkable my own are. I find this oddly reassuring and helpful when it comes to (a) keeping things in perspective, (b) taking feedback less personally, and c) avoiding the pit of despair when things feel like they are running off the rails. Reading is a great reminder that someone is always tackling something much harder and much more effectively than me at this very moment.

To finish where we started, we all want to be coachable. Like anything worthwhile, it takes hard work and some intentionality to make material improvement. Meanwhile, I’ve been enjoying working out the kinks as I’ve re-entered the world of working with an executive coach. And it really is worth the effort. As we say at Lock 8 all the time: coaching’s impact effects not only the person receiving the coaching, but also the team they lead and the organizations they drive.

A prior post explored the concept of customer effort as a critical driver of customer loyalty. That piece referenced Gartner research / articles (herehere, and here) which argued that creating an effortless customer experience — far more than raising customer satisfaction — is the key to retaining customers’ devotion. The data doesn’t lie; and I certainly buy into the concept. To a point.

On further reflection, though, I have a few reservations. These doubts are based on nuances specific to enterprise software and customers’ experience with business-to-business SaaS solutions. Gartner’s research appears to have been broad in scope; it seemingly covered customer service interactions around consumer products / services without focusing on specific industries. This post seeks to double-click into some subtleties to consider around customer effort, with emphasis on these dynamics within the B2B software environment.

1. Timing Matters: In B2B software, timing matters when it comes to customer effort. There is a fundamental distinction between the initial set-up period when the software is being implemented, versus the downstream steady-state period when the solution is being leveraged in a live environment by active end-users. For the sake of clarity, we might characterize these two phases / timeframes as “project” work (up-front) versus “process” work (downstream). Notwithstanding the rise of low-friction, freemium 2nd generation SaaS solutions, many complex business solutions still require thoughtful up-front project work. And, although the SaaS model has vastly simplified and accelerated technical aspects of software set-up, rolling out business solutions still demands organizational commitment of time and resources to do so properly (e.g. mapping processes, configuring work-flows, integrating with existing systems, and supporting user adoption). Gartner’s research in support of low customer effort appears to have excluded that start-up phase (project work) and focused primarily on downstream customer support inquiries (process work). The reality is that customers still need to invest to some degree in project work, even if their appetite for downstream process work is prohibitively low.

2. Value Matters: Building on the point above, savvy institutional software customers acknowledge some amount of up-front work is required to get great downstream value from a technical solution. And while all organizations strive to minimize that work (and time), they appreciate that effort and value are correlated. Gartner’s findings aside, customers are willing to invest in implementation efforts…so long as the downstream value they derive ultimately justifies that investment. Customer’s tolerance is a function of both variables — effort and value. Conversely, if effort and value are NOT correlated, the result will be a painful or seemingly never-ending implementation period, customer frustration, and an inevitable drop in customer loyalty. Said another way, the concept of customer “effort” is certainly relative; and customers must believe that their effort will be rewarded AND that the effort should be minimized with an easy solution to implement, administer, and use. It strikes me that all of these elements might be loosely plotted on a graph like this.

3. Timing Matters (Part Deux): There is another timing-related dynamic that encompasses both of the points above. Just as kids want to play with their holiday gifts immediately upon opening them, virtually all software buyers want to take advantage of their technology purchases as soon as possible. In other words, they want to shorten the time to value capture once they’ve contracted to use a software solution (and this is a critical metric for SaaS providers to measure). Experienced customers know that the more concentrated effort they put in, the faster they’ll get value from the solution. Conversely, a leading reason for slow or unsuccessful implementations is a lack of prioritization and effort on behalf of customers…which leads to dissatisfaction and churn. In contrast to Gartner’s research, this is case where low customer effort certainly will not translate into long-term loyalty. Note: There is also admittedly a nagging chicken-and-egg dynamic at play here; and it is worth asking whether these slow implementations would get higher priority with a more motivated customer if we vendors made them demonstrably easier to execute(?).

4. Economics Matter: There is an old saying that people don’t value the things they get for free. Without getting into a philosophical debate about total cost of ownership or open source software, it is safe to say that people’s commitment to any endeavor rises the more skin they have in the game. This is absolutely true when it comes to tolerance for project effort relating to software. Generally speaking, the less a business pays for software, the lower the willingness to invest effort implementing it. Free models command the lowest effort (virtually no skin in the game). Long-term license models (largely antiquated at this point) drive the highest. Many of us can remember a time when organizations paid huge sums up-front for a perpetual licenses…and then these pot-committed buyers would routinely have to spend years and fortunes implementing those same systems. Thankfully updated SaaS delivery and subscription models have put the onus on software providers to demonstrate value quickly and consistently, lest they risk churning the very customers they worked so hard to acquire. In any case, it strikes me as incomplete to say that low effort is unequivocally the highest determiner of customer loyalty. Rather, business model and up-front costs are other factors impacting customers’ tolerance for effort, with a related “effort curve” looking something like this:

In closing, the research on effortlessness brings an invaluable perspective to the rich topic of customer loyalty. But its application in the world of B2B software has its limits and should be applied with some caution. Specifically, while effortlessness may win the day in connection to downstream process work, delighting customers still seems to have a place in the world of up-front project work. Smart SaaS providers will benefit from understanding of customers’ journey with their solution and apply customer experience strategies accordingly. Similarly, it is important to understand a solution’s go-to-market strategy and packaging / pricing approach. Both will impact customers’ tolerance for investing effort, which should also inform the ideal customer experience. And, finally, the concept of “effortlessness” probably ought not be defined as NO effort. Instead, it is more relative in nature, where the work that needs to be done shouldn’t create unnecessary frustration. Said another way, effort is not the work itself; rather, it’s the infuriating customer feeling of “why does it have to be so hard?!” With that said, any and all customer work needs to be seamless and logical so they can derive value from their software purchases with as little effort as possible.

The key to customer loyalty is an effortless customer service experience.” These seemingly innocuous words caught me flat-footed and punched me right in the nose. I’d been focused for so long on trying to delight customers that the concept of effortlessness caught me completely off-guard.

Since being captivated by the book “Ravings Fans” decades ago, I’ve been an unhesitating proponent for striving always to exceed customer expectations. But a friend and successful entrepreneur recently initiated a conversation that has brought such longstanding beliefs into question. His perspective is informed by two Gartner articles (here and here) with supporting research that challenges the actual business impact of delighting customers…and points to (low) effort as being the strongest driver to customer loyalty. These articles and concepts caught my eye and are forcing a reexamination of some of my long-held beliefs. Below are highlights from those articles along with some accompanying thoughts and considerations.

Based on research done by CEB (2013) with 97,000 customers, the data revealed four major findings:

  1. The delight strategy doesn’t pay: As it turns out, delighted customers are no more loyal than those whose expectations were simply met — loyalty apparently plateaus once that threshold is reached. Second, it costs a lot of money to foster moments of delight for customers, which arguably makes doing so not worth it from a strictly financial perspective. And, finally, most businesses just aren’t great at creating these magic moments for customers. I’ll admit that all of these points square in the back of my head with decades of anecdotal experience.
  2. Satisfaction doesn’t predict loyalty very well: Data from the survey shows that a strong CSAT score is not a reliable predictor for whether customers will be loyal. Having implemented numerous CSAT and NPS initiatives, I know this to be true. But…I’ve also always viewed NPS as being (a) the best data we could get on customer intent, (b) useful in concert with other metrics, and (c)extremely helpful in terms of the qualitative light it shines on issues to address for various cohorts of clients. According to this study, there may be a more useful metric than NPS; more on that below.
  3. Customer service interactions drive more disloyalty than loyalty: This one was a head-turner: the research shows that a customer who requires a service interaction is four times more likely to drive disloyalty than to drive loyalty. Does this mean that the best we can hope for is to not create “raving detractors?” Maybe not…
  4. The key to mitigating disloyalty is to reduce customer effort: The bottom line is that customers hate it when they have to exert a lot of effort to solve their issue (think: calling the help-desk multiple times, having to repeat personal information to multiple service reps, getting transferred or put on hold interminably). Reducing that effort — NOT creating moments of delight — avoids disloyalty, keeps customer happy, and increases loyalty.

The article goes on to offer interesting principles of low-effort service. But the truly mind-blowing part comes in a related article that encourages companies to create effortless customer service experiences (and discourages striving to create loyal customers through exceptional customer experiences). By offering statistics on the outcome of low-effort versus high-effort experiences, the following infographic makes this case in a truly compelling manner:

Source: Gartner, Inc. (2019)

The takeaway from all of this, according to Gartner’s analysis, is that “customer effort is 40% more accurate at predicting customer loyalty as opposed to customer satisfaction.” Unsurprisingly, Gartner also introduces a metric, the Gartner Customer Effort Score, in order to measure the ease of customer interaction and resolution during a request for help.

Source: Gartner, Inc. (2020)

To determine the score, simply calculate the percentage of customers that at least “somewhat agree” (those who give a 5 or above) that the company made it easy to resolve their issue. Seems straightforward enough in its implementation, analysis, and execution of steps to address the findings.

This all resonates with my anecdotal on-ground experience; and my takeaway from all of the above is that customer effort simply can’t be ignored. And, since the CES appears to be a metric that is easy enough to spin-up without any notable disruption to the overall client experience, there is every reason to give it a trial-run. Although I’m not quite ready to completely ditch more traditional CSAT metrics like NPS and WOMI, we certainly intend to test out CES and report-back the findings. After all, getting punched in the nose once is enough to create a desire to learn from the experience.

previous post on this blog shared observations about high-stakes SaaS product development initiatives; and a follow-on piece took a deeper dive into setting related cloud services strategies. Together they focused on considerations when undertaking major SaaS product initiatives (such as re-platforming projects, new user interface introductions, infrastructure changes, functionality expansions, code re-writes, and others).

Although this post builds on those prior pieces, it steps away from the product side of things. Instead, it examines a wide range of critical, but often overlooked, “other stuff” needed to successfully introduce meaningful product changes to customers. Borrowing from the world of project management, we’ll broadly call this topic operational readiness. The harsh reality is that even a well-executed product development initiative can be greatly undermined by inadequate operational readiness. And this is often where many SaaS companies falter, particularly small-scale businesses without mature systems and processes. With that in mind, here are ten quick lessons learned and five “non-product” questions / exercises that can help organizations manage major product change initiatives.

LESSONS LEARNED:

  1. Never underestimate resistance to change: Easy to say, hard to do. We as operators are generally so much more excited about product changes than our customers are. Always respect their fear of change.
  2. Overestimate the resources your customers will need…then double it: Tip-sheets, webinars, videos, hand-holding, whatever you think customers need: they will value more than you think…and resent just as much any perceived deficiencies.
  3. Whenever you plan to introduce to the market, allow >2 months prior to train the team: Your team members need to be the experts on whom customers rely. Expertise takes time and repetition. Don’t make your team look bad in the eyes of their customers by shortchanging their opportunity to develop proficiency.
  4. Identify very clearly what the pain points are to the customer base and organize around them: Their pain of change needs to be dwarfed by the value they receive. Never confuse value to the business with value to customers — the latter is all they care about. Period.
  5. If it is everybody’s job, its’ nobody’s job: The upgrade / migration / change initiative needs to be one person’s sole responsibility to manage. Although it takes a village, that village needs a full-time, fully empowered leader in order to thrive.
  6. Communications around the initiative is a full-scale project in its own right: What gets communicated to whom, when…and how? Overinvest in this area; underinvest at your peril.
  7. Be mindful of dependencies that come up and influence other departments: This is NOT just a technical endeavor; it touches every department. If a department seems insulated from the change, you might not be thinking about it hard enough — and you’ll likely be surprised later.
  8. Establish up front how you will measure success: What is the one metric that matters most in this endeavor? The number of divergent views on this point is surprising, so don’t allow this to remain ambiguous.
  9. Determine early what, if any, ancillary tech projects / demands will emerge: Perhaps you’ll need to build an internal tool to help support migrations. Maybe you’ll need to redeploy developers to support customers. These can kill your timelines; don’t get surprised by them.
  10. Decide what to decide: What follows are thoughts on some of the important items that warrant intentional decision-making.

QUESTIONS / EXERCISES:

1. What are our “big rocks” of operational readiness?

This deceptively simple question forces companies to consider all the aspects of their offering that directly or indirectly impact how customers experience their software solution. Although there is a wide range, just a few of the usual suspects on this list include:

2. Who benefits from this project and how so?

Again, this one seems simple but warrants focused attention. The truth is that big product initiatives can take on a life of their own and cloud our understanding of their true purpose and benefit. It helps to think of each stakeholder group (e.g. customers, prospects, partners, internal team members, financial stakeholders) and even sub-sets of users (admins, super-users, casual users, executives). Then, lay-out the tangible benefit each group will derive from the initiative. These might include: a shorter learning-curve (for customers), ease of support or ability to code more efficiently (internal team), or less resource intensive implementation cycle (multiple beneficiaries, including financial stakeholders). We better have good answers for each stakeholder, or else it is going to be hard to justify to them the inevitable cost / effort it will require to adopt the proposed changes (aka: the “pain-of-change”).

3. What are the situation-specific complexities to consider?

Complexities reflect the unique nuances of each product and user-base. These are the characteristics of your business that will largely define how the company must prepare to support impending product changes. Examples of these include:

4. What are the guiding principles to be upheld?

Like any set of principles, these should represent the “non-negotiable” commitments. These may be commitments to customers or to your own organization; and they may be tacit or openly communicated. In any case, what is most important is that they are not open to compromise. Some hypothetical examples of these might be:

5. What are the operating decisions to be made?

All of the questions / considerations above play a role in organizational readiness; and companies must ask and answer a number of pragmatic questions. A few of the usual suspects tend to be:

In sum, change is hard. Operational readiness, when painstakingly undertaken and executed by a company, goes a long way toward easing that pain for its clients. Failure to do so, however, can result in tenfold the pain downstream for everyone involved.

This blog typically focuses on sharing observations from the twenty years I spent operating small-scale SaaS businesses. This post takes a different tack. It reflects more recent experiences, as I’ve transitioned over the past 18 months into the role of SaaS investor. That pivot has offered an exhilarating (and often humbling) opportunity to work with SaaS operators in a new way and from a different perspective. One of the things this experience has revealed is the need to be intentional about how investors and operators engage with each other. Failure to do so, I’ve learned, under-utilizes this potentially invaluable relationship and can lead to stale interactions. On the other hand, even a little bit of intentionality can drive more efficient and effective collaboration among company executives and board members / investors to the benefit of company performance. Below is a brief intro to the model we’ve adopted in recent months and how we’re using it to raise our game on this front.

We noticed that virtually all interactions between portfolio company executives and members of our investment team could be categorized based on two core questions. (1) Who is the owner / person responsible (portfolio company or investor) for leading a given activity or deliverable? (2) How much interaction does the exchange require? From these variables, an obvious 2x2 matrix emerged, as follows:

Because its useful shorthand to name quadrants of a 2x2 matrix, the following terms quickly attached themselves to each box.

And just as quickly, we realized that this simple schema neither represented reality, nor provided a model that meaningfully improved our communications. But, with a few tweaks, it became valuable quickly. The trick was understanding that a binary notion of ownership makes perfect sense for artifacts or deliverables but makes less sense in connection to in-depth discussions about complex topics. To recognize this reality, the 2x2 morphed into something a bit more complex; and the following model came forward:

This was a game-changer for a few reasons. First, it became easy to plot virtually all our interactions / exchanges somewhere within this model. Below is a small example with just a few of the items on which our operators and investors / board members collaborate or exchange information:

Second, this framework established some shared language, through which we gained immediate communications efficiency. It became simple, when discussing an initiative or a deliverable, to identify the box it was believed to occupy…and to quickly uncover and address any areas of misalignment. When discussing a potential topic or project, it has become common for us to rely on shorthand such as, “I think this is a Box 4 topic, do you agree?” This has squeezed-out some previously existing room for confusion. To avoid all doubt, we use the following numbering system:

But the biggest benefit by far has been to raise our awareness of the amount of time and energy spent in each box…and our sensitivity to wasting time in the wrong box on a given topic. For example, in the first few months after an investment, we spend a good deal of time in collaborative discussion (Box 2: Shared Strategic Planning). That makes a ton of sense for many reasons, particularly during a period where there is a lot of shared learning around complex topics and where planning occurs through a collaborative and iterative process. But that can be really time consuming. And, as the company moves into more of an execution mode, it becomes advantageous to migrate operator-investor interactions more into boxes 4–7. When recently asked by a portfolio company CEO about a particularly thorny product-related issue, I reflexively suggested that we get in a room to discuss. Instead, he responded, “In this situation, it would be more valuable for me to hear a summary of your lessons learned on this topic, can we just make this a Box 5 presentation from you guys?” I was happy to comply; since we are all aligned around optimizing company performance. This kind of directive request helps us to arm operators with whatever support they need to succeed in the market.

This whole approach reminds me a bit of the balanced eating plate graphics that we learned about in Health class as kids. The general concept is timeless, even if the exact categories and proportions will forever be a subject to ongoing examination and debate.

In both scenarios, what’s most important is that there is (1) a healthy balance, (2) a framework for making good, intentional choices, and (3) a useful check against simply defaulting to the part of the plate — or the type of interaction — that satisfies our craving in a given moment. Finally, as the saying goes, variety is the spice of life. Our experience is that the same is true when it comes to interactions between operators and investors — a little planning and a bit of balance / diversity leads to more efficient and effective interactions that are also just generally easier for everyone to swallow.

It’s easy for leaders to get caught up in the day-to-day of running small-scale businesses. Particularly during challenging times, it can take all our energy just to “keep the wheels on the bus.” Unfortunately, a casualty of operating in this mode is that we tend to focus far less on the long-term composition of the team — who’s actually on the bus, whether they are in the right seats, and who should be getting on / off at upcoming stops. This is hardly surprising — such planning demands both discipline and foresight. It’s also difficult to get right: organizational design is quite complex, and according to research from McKinsey & Company, less than 25% of organizational redesigns succeed. With that in mind, this post can’t begin to scratch the surface on this rich topic. Rather, it simply introduces a quick-and-dirty exercise to help leaders elevate and think proactively about their organizational “bus” both now and in the future. What follows is a description of the exercise (the “What”), some tips around its execution (the “How”), and some observations about its effectiveness (the “Why”).

The What: The exercise is quite simple and builds upon something that virtually every organization already has available in some format — a current org chart. Using that as a starting point, the leader creates a series of hypothetical future org charts for the business. Specifically, (s)he creates four new / additional org charts, each representing successive six-month intervals into the future. This results in a total of five prospective org charts, essentially five snap-shots that look forward two years, six-month at a time. The five org charts are as follows:

The How: This really is a simple exercise, so there is no need to overthink it. But a few pro-tips can’t hurt; and the following will help make the exercise even easier and more impactful:

The Why: The primary benefit of this exercise is hopefully clear: it is a low-effort way for a leader to plan out with intention and purpose how an organization will grow over time. It works well because it doesn’t require any special skills, resources, or training; and it is something leaders can easily do on their own a couple times of year with a moderate amount of discipline in a short period of time. A few of the side-benefits, and why this exercise works in achieving them, are outlined below:

In closing, this exercise is largely about interdependency between the business outcomes and the people-related aspects of organizations. Leaders generally have a keen sense from a mission and financial perspective of where they want their businesses to be at various points in the future. What we tend to be less good at is identifying and aligning the roles and skillsets necessary to achieve those objectives. Yet, they are completely interdependent — the envisioned goals, and the difficult-to-define team / structure required reach them. This exercise aims to help navigate the organizational side of things. Hopefully, it can help leaders develop a far-seeing view of who should be “on the bus”…and provide everyone a much smoother ride toward the desired destination.

Are we speaking the same language? Let’s talk.

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