Many say sales is a numbers game. For me…the longer I do this work, the more I’m convinced that at least for complex enterprise sales, it’s a people-and-purpose game…and the numbers follow.
And frankly it’s just as true for selling shoes at LL Bean. I know, I’ve done it.
In a recent conversation (Thoughts on Selling podcast #65) with fellow sales transformation leader Tracy Linne, we dig into what it really takes to build sales organizations that don’t just hit quota once, but learn, adapt, and sustain performance. The thread running through it all: purpose that people can feel, and cultures built on trust.
From “Fixing” to Building What Sticks
Tracy calls herself a fixer. Not the Hollywood version, but instead the kind who lands, diagnoses, and helps leadership rebuild the system so it actually works. Sometimes that means building a go-to-market engine from scratch: new motion, new people, new process, new tech. Other times it’s a turnaround: the company is ten years in, stuck under $10M ARR, tired of heroics and misses, and ready to get honest about the gap between how they think they sell and how customers actually buy.
The move that separates a real fixer from a fire drill? Day-one clarity and day-one candor. Those first 90 days are about calling things the way they are, aligning a founder or exec team around reality, and co-creating a path forward that the whole org owns. Not “my plan” — our plan. Without that shared purpose, everything else becomes motion without momentum (kinda like a pinball ricocheting around the board).
The Pillars (In the Right Order)
We all know the trio: people, process, technology. Most teams nod along, then skip straight to buying tools. The truth is, tech simply amplifies whatever culture and process you already have. If you’re misaligned, tools help you fail faster.
Tracy’s hierarchy is both blunt and on-point:
- Customer first. What problem are we solving, for whom, and how do they know it’s solved?
- Team second. Do we have the right people, in the right roles, playing to their strengths?
- Everything else flows from there.
That order forces hard conversations about how you sell, who you sell to, and how your team needs to evolve. It also stops a lot of unhealthful “tool-flavored” debates.
Selling as a Team Sport
One simple shift creates outsize impact: treat sales like a team sport. Bring product, marketing, finance, and execs into real deals—not to crowd the rep, but to widen context and shorten cycles.
Run key workstreams in parallel rather than in series (security, legal, procurement, internal champion enablement), and you’ll often shave 20–25% off cycle time while improving deal quality.
The side effect is powerful: when more eyes are on the work, the forecast gets honest. Wins and risks are socialized early. The org learns what “good” looks like…and what sandbagging and wishcasting look like too.
Pricing, Positioning, and the Courage to Change
One theme we both keep running into: companies trying to sell enterprise-impact solutions as low-ticket “velocity” plays because investors want quick logo acquisition. While It may feel good in the short term, this approach will eventually kill you. If your product actually solves a cross-functional, high-pain problem, price it and position it to match. Yes, you’ll add 45–60 days and need an extra signature. You’ll also drive retention, expansion, and profit — and stop replacing yourself every year.
While that decision takes nerve and alignment, the market rewards clarity of value.
Measure What Matters (and Separate It)
Many CRMs still tie stage to probability. Move to Stage 3? Auto-jump to 60%. It’s convenient—and misleading. Uncouple them. Let reps state their confidence independently. Then obsess over conversion rates by stage and time-in-stage. That’s where you find the real friction: messaging gaps, misread deals, or process debt that slows everything down.
When you fix conversion and velocity, you don’t just close more — you waste less. A dollar spent on adding MQLs never beats a dollar spent improving stage-to-stage flow.
Personalization That Actually Helps
Intent data is useful. Personality data can be a force multiplier. Tracy uses tools like personality modeling (e.g., from public profiles) to tailor conversations and follow-ups to the human beings on the other side of the Zoom room. Analytical operator? Lead with structure, outcomes, timelines. Relationship-first leader? Start with trust and context.
No tool replaces curiosity!
One of my favorite coaching moments: a coaching client, an enterprise rep for a large tech company, studied two stakeholders’ LinkedIn pages and noticed they’d each been at the client company for over twenty years.
She opened the meeting with a simple, human question: “You’ve each been here over two decades — what keeps you here?” That launched a twenty-minute conversation that led directly to an introduction to the CDO. Tools surface signals. Curiosity turns them into connection.
AI Won’t Replace You — But It Will Expose You
Yes, AI is changing the stack. It will automate more “busy work” than most teams expect. Early-career sellers worry about being replaced. My take: AI is a ladder, not a trapdoor. If you let it handle the repetitive parts, you can climb toward the work only humans do well — listening deeply, diagnosing honestly, crafting narratives that mobilize organizations, and negotiating with empathy and backbone.
If your idea of prep is copying and pasting a bot’s summary without understanding the business, the person, or the politics? AI will expose that, fast. The bar is going up, not down. And…if you bump into a prospect without warning, you will have to be prepared to “wing it.” No time to pull out your phone and consult with ChatGPT!
The People Pillar You Can’t Ignore
Here’s the leg of the stool most leaders underinvest in: a data-driven view of your team. We measure leads, pipeline, win rates — everything but the humans doing the work. You can (and should) blueprint your team with light-lift assessments that reveal behavioral strengths, coaching gaps, and role fit. It’s not about labeling people; it’s about placing people.
Thinking about a reorg? Don’t rearrange boxes on a hunch. Use data to inform who thrives in complex net-new versus who excels in expansion vs. who belongs in customer leadership or enablement. Then pair that with real coaching. (Yes, leaders coach. Or they develop someone who truly does.)
The Daily Reset — and Ownership
Culture isn’t a slide; it’s a daily practice.
The most practical advice both Tracy and I share with reps and managers is simple: start your day with purpose. Whatever sets your mindset — workout, writing, quiet time — do it consistently. It changes how you show up to the first call, the forecast review, the tough conversation. And if yesterday went sideways? You get a reset every morning. Use it.
Ownership looks the same at every level. Reps who embrace sales as a profession — not a stopover — lean into feedback, get curious about the craft, and build what I call a relationship bank account with customers and managers alike. Funny enough, the shortcut to career longevity isn’t gaming the comp plan; it’s making your manager look good by being reliable, honest, and proactive. That builds a reputation you can’t buy.
Five Moves to Build a Culture of Trust and Growth
- Tell the truth early. Diagnose your current state with candor. Align the exec team on reality before you chase the future.
- Reorder the pillars. Customer → People → Process/Tech. Buy tools last, not first.
- Run deals as a team. Parallel the workstreams, shorten cycles, and make the forecast a shared artifact rather than a solo performance.
- Measure the middle. Separate probability from stage. Obsess over conversion and time-in-stage. Fix bottlenecks with surgical changes.
- Personalize with purpose. Use AI and personality insights to augment — not replace — human curiosity. Earn trust by speaking each buyer’s language of value.
Purpose isn’t a poster stuck on a breakroom wall; it’s the thing that keeps people moving when change gets uncomfortable. Trust isn’t a feeling; it’s the compounding effect of a hundred honest actions — how we scope, price, forecast, and follow through. When you put those two to work, growth isn’t a surprise. It’s the natural byproduct of a culture you built on purpose.