A Teaser: The Awkward Teenage Years of B2B SaaS
Key shifts from pre-revenue to $30M+ in ARR
Over the past decade, I’ve had the pleasure of working in executive roles spanning go-to-market, operations, customer experience and M&A for B2B SaaS companies ranging from $5M to $30M in ARR - both private equity and venture capital backed, alongside founders and professional CEOs. For those who have experienced this journey, these can be awkward (yet critically important) teenage years for B2B SaaS.
All stages have their challenges. In the pre-revenue or “0-to-1” stage, there’s no data, no case studies; just a concept of a product, belief in the mission, and your ability to will that belief into existence. Post $30M, and you’re up against more complexity, management of larger teams, TAM expansion pressure, sometimes global operations. $5 to $30M? It’s the awkward middle. It’s not small or nimble enough where success can ride the backs of a talented entrepreneurial founder. It’s not big enough where the benefits of scale really start to take effect. So, how do companies come out of those awkward teenage years growing predictably and profitably? How do you scale without scale? How do you keep the agility of a startup while forming the discipline of a company built-to-last?
Every company is different - different products, different industries with varying buying behaviors and competitive landscapes, different teams and cultures, different growth potential, etc. This means the approach and execution will absolutely vary, but in my experience there are a set of common issues companies at this stage inevitably must navigate and transform through. I’m not referring to the run-of-the-mill departmental issues like demand gen strategy, sales pipeline management, product roadmap planning. Rather, these are company-wide, cross-functional issues that the CEO and executive team should be naming and addressing. Exactly which issues are relevant and in what sequence is unique to each company. Each of these topics warrant deeper dives, and my goal in this series of posts is to equip you with “headlights” into what potential issues to get in front of, why they’re important, and a perspective on how to approach those issues.
For now, let’s get a starter list of key shifts during these awkward teenage years and questions that may help you identify the issues that matter to you, whether you’ve encountered them in the past, present, or future.
Culture & Team
From Small to Big(ger) - are you innovating or making decisions slower than you have when you were smaller? Do you worry that getting bigger will mean the loss of an entrepreneurial start up culture? // You’re not that big - preserving agility and “small” culture while scaling your SaaS business.
From I Do to You Do - do you find yourself as a bottleneck in decisions? Are you worried that others won’t be able to drive the same decisions or initiatives that you can? // The mindset shift for founders and realization that there’s an enablement problem
From Many Hats to Right People Right Seats - are too many generalist cooks in the kitchen as you scale? Are you facing decisions on when, where, and how to augment your team with specialists? // The role of specialists as you scale on a base of generalists
Operations & Product
From Instinct to Data (and Instinct)-Driven Insights - are team members able to leverage a combination of data and “gut” to drive decisions? Do you feel caught between the need to be more data-driven but having an absence of reliable data? // Building the GPS for your B2B SaaS business.
From Sales-led to Balanced Sales & Product - is it becoming harder and more costly to deliver quality customer support across customized deployments? Do big customers have an outsized impact on product roadmap? // Break the sales-led scalability spiral.
From Feature Development to Product Management - are team members and customers able to articulate the value your solution drives for customers? Are you struggling with team members celebrating when features ship, only to find that there’s bugs, or don’t really solve the customers’ problems? // The shift from developing features, to driving outcomes
From Surviving to Managing Metrics That Matter - do you catch yourself or the team making decisions for short term survival? Are you saying yes to too many bad fit sales opportunities or making too many concessions? // Operating in a survivalist mindset, and the damper it puts on enterprise value
Go-to-Market
From Discovering ICP to Focusing ICP - do team member express the same ICP? Are customer problems, needs, and business cases for your products & services wildly variable? // The opportunity cost of leaving the door open on ICP
From Founder-led Sales to Repeatable Sales - are you having trouble demonstrating predictable sales and pipeline to your board? Has a seller closed a deal with minimal assist from a founder? // Codifying the magic from founder-led sales
From Honing Your Market to Upmarket / Downmarket - are you getting pressure to go upmarket to increase ACV or retention? What about going down market to drive more predictable TAM? // Beyond “repackaging” - the true investment to swim up-market or down-market.
From One Product to Cross-Selling - are you evaluating new product capabilities to take more wallet share of your customers? Are you missing your cross-sell targets? // Cross-selling, the sexy killer
From Customer Support to Customer Success - is customer retention an issue? Are you having challenges upselling or expanding accounts? // The transition into “true” Customer Success.
From Individual Heroics to Scalable Customer Success - do you find a frequent need to point the same SMEs and product experts to triage and solve customer problems? // Driving repeatable and scalable operations.
M&A
From Our Product to Our Platform - are you considering M&A in the future and don’t know how to prepare? Are you dealing with the fall-out of a poorly executed M&A integration? // Laying the groundwork for M&A.
There it is. A good starter list for now. Not much insight quite yet but my hope is that there are a few issues you’ve identified that stand out to you, and even a couple that aren’t captured above. If you have ideas, I’d love to hear them. Otherwise be on the look-out for follow-on posts to come that begin to knock these out. Happy scaling!
Executives, founders, operating partners - what challenges are you facing in scaling your B2B SaaS business? Post in the comments!