The B2B SaaS Sales Narrative

VP Sales at B2B SAAS - Autobiography.pdf

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When I was working in customer success at a B2B SaaS company, I spent a lot of time at the intersection of different teams. I'd sit in on handoff calls with sales, troubleshoot implementation issues that traced back to the sales process, and watch renewal conversations unfold. The more I saw, the more curious I became about how the entire sales function actually worked. Not just the mechanics of closing deals, but the organizational design, the evolution from startup to scale-up, and the hundreds of small decisions that separate high-performing sales teams from struggling ones.

The problem was, most of what I found online was either too tactical ("10 cold email templates that convert!") or too theoretical (dense textbooks that felt disconnected from reality). I wanted something in between: a cohesive narrative that explained the why behind the what, told from someone who'd actually been through multiple growth stages and could share the hard-earned lessons.

So I decided to create it myself.

What I Built

I used Claude to generate a long-form playbook on B2B SaaS sales, written from the perspective of a VP of Sales with 20+ years of experience. The idea was to create something that reads less like a manual and more like a candid conversation. The kind of wisdom you'd get over coffee with a seasoned exec who's seen it all and isn't afraid to tell you how it really works.

The document covers:

• How sales evolves from founder-led chaos to a mature, global operation

• The different roles that emerge (BDRs, AEs, SEs, CSMs, Sales Ops) and how they work together

• The end-to-end customer journey across SMB, mid-market, and enterprise segments

• Go-to-market motions: inbound, outbound, PLG, and account-based selling

• Compensation structures, quotas, and how incentives shape behavior

• The tools and infrastructure that become mission-critical as you scale

• The real metrics that matter: pipeline coverage, conversion rates, CAC, LTV, NRR

• How sales interacts with product, marketing, finance, and customer success

• The hard truths that only come with experience

  
  

What I Particularly Liked

A few sections really stood out to me:

• The section on founder-led sales resonated because it captures something I saw firsthand: those scrappy early days aren't just about closing deals. They're about discovering product-market fit through direct customer contact. You can't skip that phase.

• The discussion of customer journey differences between SMB, mid-market, and enterprise was eye-opening. I knew enterprise sales took longer, but I didn't fully appreciate how fundamentally different the processes are - from buying committees to procurement nightmares.

• The cross-functional dynamics section. The sales-CS handoff problems, the sales-product tension around features, the sales-marketing debate over lead quality. I've lived all of these. Seeing them named and explained with solutions was validating.

• The "hard truths" section is probably my favorite. Things like "scaling too fast is worse than scaling too slow" and "churn tells you the truth" are the kind of lessons that only come from scars. This isn't theory. It's pattern recognition from someone who's been burned and learned from it.

How I Made This

For anyone curious about the process, I used Claude Sonnet 4.5 to generate this document. Below is the full prompt I used. I wanted to see if I could create something genuinely useful and comprehensive by being very specific about the structure, tone, and depth I was looking for.

The result exceeded my expectations. What Claude produced felt like it came from a real person with real experience. Because the training data it learned from includes countless real experiences, synthesized into a coherent narrative.

Whether you're in sales, thinking about getting into sales, or just trying to understand how this critical function works, I hope you find this useful. I certainly learned a lot by creating it.

The Prompt I Used

"Write a long-form, candid, and deeply practical playbook on B2B SaaS sales as if narrated by a Head of Business Development with over 20 years of experience. The article should not read like a textbook or a list of tips but as a cohesive narrative that explains how the sales function in a SaaS company evolves from the founding stage, when sales are founder-led, through early scaling, growth, and into a mature global operation. The story should show how sales is not a single role but an interconnected system of people, processes, and incentives that must evolve as the company grows. Introduce the different roles that emerge in a sales organization — business development representatives, account executives, sales engineers, customer success managers, account managers, sales operations, and leadership — and explain how each function adds value, collaborates with others, and matures with time. Narrate the end-to-end customer journey, from lead generation and qualification to discovery, demos, proof-of-concept, negotiations, closing, and renewal, showing how this process looks different for SMBs, mid-market, and enterprise clients. Weave in discussions of go-to-market motions — inbound, outbound, product-led growth, and account-based selling — and explain when and why each approach works. Describe the role of compensation structures, quotas, commissions, and incentives in shaping sales behavior, and how those evolve across company stages. Discuss the key tools, CRMs, and analytics infrastructure that become essential as the company grows, distinguishing between what’s “nice-to-have” versus mission-critical. Use a candid tone to highlight the real metrics that matter — pipeline coverage, conversion rates, sales velocity, CAC, LTV, and net revenue retention — and why obsessing over the wrong numbers derails teams. Pay special attention to how sales interacts with product, marketing, finance, and customer success, explaining both the friction points and the best practices for alignment. Throughout, weave in hard truths and lessons that only come with experience: why early sales hires make or break momentum, why scaling too fast can backfire, why procurement cycles in enterprise sales are brutal, and how to know when to pivot your go-to-market strategy. The narrative should be engaging, slightly memoir-like, but always focused on actionable insight — the kind of field-tested wisdom that strips away buzzwords and tells the reader “here’s how it really works.” Conclude with a reflective section synthesizing the journey: what B2B SaaS sales ultimately teaches about building trust, creating systems, managing people, and scaling organizations."

Have thoughts on this? Disagree with something in the playbook? I'd love to hear from you. Drop a comment below or reach out.