From “make it happen” to “make it matter”: 6 hard-won lessons from my chat with on building companies, careers, and reps that thrive in 2025

Introduction: the drink that changed the conversation

Two years ago, John Barrows and I grabbed an impromptu drink on Mission Street after Dreamforce. We should have been celebrating. Funding was cheap, growth was up-and-to-the-right, and everyone on LinkedIn was shouting “rocket ship!”

Instead, we compared bruises. I had just executed my first layoff. John was retooling his business after a brutal market swing. Over warm IPAs, we asked an uncomfortable question:

“What happens when you feel like you work for your own company instead of leading it?” – John Barrows

Fast-forward to our latest Make It Happen Mondays episode. Same two humans, but the energy is different, less whiplash, more forward momentum. The conversation ran 65 minutes and spanned layoffs, AI agents, the “give-a-factor,” and whether reps should run back to the sales floor. Below is the field guide I wish I’d had when the world tilted sideways.

1. Rediscovering pride: the CEO’s first KPI is feeling the product

“There was a day I woke up and realized I wasn’t proud to demo my own platform.” – Melanie

When the Series B funds cleared in December 2021, Spekit went from “scarcity scrappy” to “hiring spree.” The dashboards said growth; my gut said bloat. I’d stepped out of design reviews, stopped listening to support tickets, and found myself asking permission to join meetings inside a company I founded. Pride evaporates quietly; you notice only when it’s gone.

What changed

• I put myself back on the demo calendar every week. Nothing surfaces friction faster.

• We replaced “more features” with a “no PRD, no ship” rule: if the problem, hypothesis, and success metric weren’t crisp, the sprint halted.

• I measured my energy the same way I measure MRR: trending up or right-sizing down.

  
  

Takeaway: Whether you run a team of 10 or a pipeline of one, feeling proud is a lead indicator. If the thought of showing your work to a customer makes you flinch, fix that first. Revenue follows quality, not the other way around.

2. Trust is everything, until it isn’t

Both John and I hired executives who we later had to unwind. The pattern:

1. Market was frothy → we hired fast to “keep pace.”

2. “Hire great people and get out of their way” became an excuse for disappearing context.

3. Six months later, we were trapped in politics, misalignment, and cultural rot.

   
   

“You should be intimidated by the quality bar, not by my presence in the room.” – Melanie

The rubric we use today

Question	Red flag	Green flag
Do they earn trust or assume it?	“I’ll need full autonomy.”	“Let’s define the guardrails together.”
Will they challenge my thinking?	Agrees too fast.	Pushes back with data + empathy.
Do our values match under pressure?	Blames “market conditions.”	Describes their own post-mortems.

Takeaway: Delegation without inspection is abdication. Depth reviews, call listening, and shadowing are not “micromanagement” they’re how leaders protect the standard.

3. Pivot, persevere, or pass the baton?

Every founder (or seller) hits the identity wall: Am I still the one? The shortcut is joy. If the work that once lit you up now drains you, investigate. For me, the grind signaled a role mismatch, not a mission mismatch. The solve was hiring a COO (if you don't know Seth McGuire, you should) to run go-to-market while I went back to product, narrative, and customers.

John calls it the Stage Rule:

• Stage 1 (0-$5M): chaos junkies

• Stage 2 ($5-$20M): process scalers

• Stage 3 ($20M-IPO): enterprise orchestrators

Very few humans love all three.

Takeaway: Inventory your energy, not just your skills. If the tasks that once fueled you now flatten you, it’s time to narrow focus or change seats before the market does it for you.

4. Hard markets don’t kill reps, mediocrity does

“I’m optimistic for anyone willing to put in the work. I’m not optimistic for people going through the motions.” – John Barrows

John and Melanie’s survival playbook for 2025 reps

1. Get back in the pit: Remote selling is here to stay, but early-career reps need osmosis. If you’re plateauing, spend two quarters sitting shoulder-to-shoulder with closers.

2. Sell something you believe in: Enthusiasm is still the fastest data-transfer protocol. If you can’t glow when you talk about the product, change products.

3. Master the boring fundamentals: Discovery, critical listening, and deal hygiene feel “old school” until pipeline stalls. The AI agent that writes your recap can’t replace the question you never asked.

4. Measure your give-a-factor: Can your manager see that you care? Effort shows up in call research, CRM notes, and follow-up speed long before the deal closes.

   
   

5. AI is the assistant, not the answer

The middle third of the episode deep-dives on cognitive overload. Reps drown in release notes, feature decks, and competitor alerts they’ll forget by Thursday. Enter just-in-time enablement:

“You only need to know what you need to know, exactly when you need to know it.” – Melanie

Three principles for AI-powered enablement

Principle	Old playbook	Just-in-time playbook
Context > content	Send the deck to every prospect.	Surface a nonprofit case study when Salesforce field = “501(c)3)”.
Less > more	Quarterly “megatrainings.”	Bite-size nudges before or after the call.
Capacity > coverage	Cram everything into onboarding week.	“Everboarding” triggered by role, stage, or trigger word.

What it means for sellers: AI will eliminate data entry and surface relevant intel, but it can’t manufacture curiosity or critical thinking. The reps who win will pair machine-fed signals with human-led questions.

6. Quality is the new quantity

LinkedIn, email, and even cold calls have become a volume game, and it shows. The inbox glaze is real. Both John and I believe the pendulum is swinging back:

• Reps: fewer, richer touches outperform sequences on autopilot.

• Leaders: shipping one lovable product beats five “MVP-ish” widgets.

• Enablement: a single playlist that reps actually finish crushes ten forgotten courses.

“We need to do less with less, not more with less.” – Melanie

Scorecard for the quality era

Discipline	Quantity metric	Quality metric
Outbound	100 emails/day	30% reply rate
Product	Features shipped	Features adopted >60%
Enablement	Hours of content	Win-rate lift vs. control

Final word: make it matter

The last thing John said before we killed the recording was simple:

“Go make somebody smile today.”

That’s more than a feel-good sign-off; it’s an operating system. Pride, trust, focus, craftsmanship. None of it sticks unless people feel it.

So here’s your six-point checklist:

1. Audit your pride: Would you buy from you?

2. Inspect trust: Does every hire lift your standard?

3. Follow energy: Role, stage, or seat, match the work to the joy.

4. Raise your rep game: Fundamentals + intentional environment.

5. Embrace AI as a teammate: Offload noise, keep the thinking.

6. Choose quality over the comfort of quantity.

If you tick those boxes, the uncertain market looks a lot less scary and infinitely more exciting.

Be sure to follow the Make it Happen Mondays podcast for more of John's raw conversations, DM me if you want to jam on any of these ideas or see how Spekit turns them into repeatable habits inside your revenue team’s workflow.