Crossing the post-sale chasm: How post-sale teams can help their company scale to $100M+

Eventually, every fast-growing startup becomes the struggling victim of its own success, and own success team. The tactics that worked so wonderfully to onboard and retain customers while you grew from $0-$10M suddenly begin to fray. The lack of structure that your early adopters hailed as “highly personal service” no longer scales—yesterday’s innovation is now the very thing that’s causing inefficiency, frustration, and churn.

These are growing pains every startup faces and nowhere are they more predictable, destructive, or avoidable than among post-sale teams. However, in this insight, there is hope.

I define “post-sale” as the collection of activities that follows the sale at an enterprise software company. The term encompasses customer success, but it is not synonymous with it, because it also includes implementation, professional services, customer education, support, and more. It’s a broad set of functions, inconsistently defined and in my experience, lacking in best practices and professional development resources. These leaders are often masters of figuring things out on the fly. They possess an encyclopedic knowledge of their customer and are an irreplaceable part of the company. But what if their past experience doesn’t provide them the skills, visibility, or foresight needed to continue supporting the company’s growth?

I’ve begun to realize these post-sale growth issues tend to occur at predictable intervals for predictable reasons. This suggests something can be done, and it’s raised a question I cannot stop thinking about: What do fast-growing startups stand to gain if, with a bit of help, the post-sale leader who’s clever enough to take them to $10M is suddenly clever enough to also take them to $50M and then to $100M?

Crossing the post-sale chasm

In dissecting this problem, I’ve realized Geoffrey Moore’s great contribution to the understanding of how startups acquire customers works just as well for supporting and nurturing them after the sale. Below is an unabashed homage to his work that explores the phases I believe companies tend to go through.

Each phase is defined by a common set of experiences. In each successive one, post-sale leaders deal with a growing number of challenges of increased complexity. More challenges multiplied by more difficulty tends to create a situation where no one could possibly be successful without committing a lot of errors or having been through it before. Hence why so many startups struggle to cross their post-sale chasm (or transition through these phases without significant leadership turnover).

No one post-sale leader can be an expert in all things post-sale. Just as every marketer has specialty agencies for design, operations, and content, so should post-sale leaders be able to supplement their strengths with complementary partners, consultants, or training.

But what if we did more to take that knowledge sequestered at higher levels of growth and relay it to leaders at earlier phases? What if there was more mentorship, best practices, and guidance so that when that $0-$10M leader needs to start charging fees for implementations or create specialized teams to handle SMB and enterprise clients, they have a play they can run? Or when a big new client who’s working with a delivery partner posts something inflammatory in the community, they know exactly how to manage the fallout?

What if we actually armed these leaders with the knowledge and resources to develop in those key transition areas so they’re the ones who continue to drive the company to $50M or $100M without missing a beat?

To say this idea is exciting to me would be a vast understatement. After long consideration, I’ve decided to pursue it full time.

Hello, CCO

I feel compelled to preface my announcement of my new consultancy by saying that I most certainly do not have all the answers. I’ve started HelloCCO in pursuit of more perfect answers. But what I can say is that I’ve been a post-sale leader at three companies that have seen this fast growth and had billion-dollar exits over the last decade—RingCentral, Marketo, and most recently, Gainsight. I have been lucky enough to cross the chasm at each phase, always with the help of others. Now, I’d like to create resources that help other post-sale leaders navigate their own crossings.

The HelloCCO mission is simple: To provide transitional guidance to help your post-sale organizations scale. I’ll work alongside CEOs, their post-sale leaders, and investors to capitalize on opportunities to increase net dollar retention, improve client onboarding, expand product adoption, and grow margin.

Specifically, I see the benefits this way:

  1. Accelerated time to value—design onboarding experiences that are impactful, repeatable, scalable, and help clients realize value faster.
  2. Increased net dollar retention—measure and improve account health and growth.
  3. Insights that drive upsell and growth—conduct Win-Loss and Churn-Expansion analysis.
  4. Expanded product adoption—identify the sticky, high-value solutions that deliver an ROI.
  5. Delightful end-to-end customer experiences—help clients thoughtfully design the activities, handoffs, and touchpoints throughout the entire post-sale journey.

What do fast-growing SaaS companies have to gain from getting their post-sale chasm crossing right? So much more than I think they even realize, and that’s something I hope HelloCCO can help them realize through our consultancy.

This article is the first of what I hope are many, and I would love your raw and honest feedback. And if you see me posting on LinkedIn about these topics, please do say hello. 👋🏻

Rod Cherkas

Rod Cherkas is a well-respected consultant, advisor, author, and speaker. He has been a post-sale executive at several of the world’s most customer-centric companies including Intuit, RingCentral, Marketo and Gainsight. He is the founder and CEO of HelloCCO, a strategy consulting firm that partners with innovative companies across diverse industries to develop, execute and scale strategies for their customer-facing functions. His clients rave about their “repeatable results with Rod”.

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