The other day, I had the opportunity to speak with the Chief People Officer at a mid-sized private equity firm, who supports portfolio companies in strengthening talent, leadership, and human capital capabilities that drive long-term value creation.

This person’s perspective is shaped by unique business experiences by any standard. Before joining this firm, the person served at a technology company, helping guide the company through private equity ownership, global expansion, and extraordinary growth.

During their tenure, the company nearly tripled in size, improved retention by more than 40%, increased employee engagement by 30%+, earned multiple Great Place to Work recognitions, and was repeatedly named among the fastest growing private companies in America.

One observation from our conversation stood out. Revenue problems are often diagnosed as sales problems when they are really people and process problems. Great HR leaders help define expectations, accelerate onboarding, coach managers, improve retention, and build the accountability systems that allow teams to perform consistently.

Training without reinforcement fades. Culture without accountability disappoints. Sustainable growth happens when people know what winning looks like and have the support to achieve it.

How many of your reps hit quota last quarter?

When the people system is loose, the number rides on a couple of names. Quotas get set on hope. Coaching turns into deal inspection. Accountability shows up only after a miss.

The result is the same every quarter: the number becomes a surprise instead of a planned outcome. In 2024, 69% of B2B reps missed quota (Ebsta 2024 B2B Sales Benchmarks). The fix is rarely more pressure. It is better infrastructure.

As you read this workshop, consider one question: is your revenue team asking people to succeed through effort alone, or have you built the infrastructure that helps them win repeatedly?

50% more likely to hit quota when reps get consistent coaching Source: MySalesCoach, State of Sales Coaching 2025

The infrastructure is the multiplier. When 17% of reps generate 81% of revenue (Ebsta 2024 B2B Sales Benchmarks), the gap is structure, not talent. Build the quota, coaching, and accountability system once, and the whole roster moves toward the top of the curve instead of leaning on two names. 

Key Terms

Do's and Don'ts

This Week's Challenge

Pull your quota attainment by rep this week, mark how much of the number rides on your top two names, and book one coaching block to start closing that gap.

Your best CSMs block an hour before the strategic QBR. They pull NPS trends, dig through support history, check adoption deltas, draft the deck. The customer feels seen.

The other 190 QBRs this quarter don't get that hour. The CSM scans the dashboard five minutes before the call. The customer answers the same baseline questions again.

Viktor changes that ratio. Before any QBR, message Viktor. He pulls account health, open tickets, product usage, and recent company news. Drafts the brief. Attaches the deck. Posts it in your DMs before the day starts.

Every CSM walks into every QBR prepared. Even when there are 200 of them.

20,000+ teams. Connects to Gainsight, Zendesk, Salesforce, and 3,000+ other tools. SOC 2 certified.

Get Started for Free

Own Your Number

Quota lands on your desk and it can feel like a verdict. It is not. It is a target you can attack with a plan, the same way you attack an account.

If your number depended only on the one skill you avoid most, would you still hit it?

EXAMPLE  A CTV seller at a regional broadcaster kept missing quota by a hair. The gap was not effort. Every deal stalled at the same place, the budget conversation, and she had routed around it for a year.

Step 1  Find the gap. Review one real deal that slipped this quarter. Name the single moment it slowed, in one sentence.

Step 2  Drill it on purpose. Pick that one skill and work it on your next five live calls. Development you control shows up in the number first.

Step 3  Coach yourself when no one else does. Use call recordings, a peer, and the deals in front of you. Waiting to be coached is a choice to stay flat.

Q.  What if my quota is genuinely unrealistic?

A.  Bring evidence, not a complaint. Show your pipeline coverage and win rate, and ask for a quota built on math you can both see.

Coach on a Rhythm

Most managers inspect deals and call it coaching. Inspection moves a deal this week. Coaching moves the rep for every deal after.

In your last one-on-one, did you build a skill or just update a close date?

EXAMPLE  A sales manager at a radio group ran sharp pipeline reviews every week. The forecast was clean. The team still flat-lined, because no one ever worked on how the reps actually sold.

Step 1  Split the meeting. Ten minutes on the forecast, twenty on one skill per rep. Protect the coaching time before the week eats it.

Step 2  One skill per person. Pick a single skill for each rep and stay on it. Consistency beats intensity. Reps who get consistent coaching are 50% more likely to hit quota (MySalesCoach, State of Sales Coaching 2025).

Step 3  Make the rep own the next move. End every session with the rep naming what they will do. You coach the thinking, they own the action.

Q.  How do I coach when I am carrying my own number too?

A.  Pick three reps and a fifteen-minute slot each. A small rhythm you keep beats a big plan you abandon.

Build the System

When the number rides on two names, you do not have a sales team. You have a dependency. Infrastructure spreads the load across the whole roster.

If your top two sellers left this week, how much of next quarter walks out with them?

EXAMPLE  A regional publisher set every quota at last year plus fifteen percent. Half the floor missed, the best two reps carried the rest, and when one left, the quarter cratered.

Step 1  Set quotas on evidence. Build the number from pipeline coverage and ramp reality, not last year plus a hope.

Step 2  Coach on a rhythm. Require a weekly coaching block from every manager, then inspect that it happens.

Step 3  Make accountability visible. Write the expectation, the evidence, and the consequence on one page everyone can see. When the number leans on a few names, the answer is structure, not heroics.

Q.  Where do I start if all three are broken at once?

A.  Start with quota math. A realistic, visible quota makes coaching and accountability mean something. Without it, both are guesswork.

Recommended Reading

  ==

The Revenue Workshop isn’t theory. It’s a field-tested system used by real leaders, in real markets, under real pressure.  

Each newsletter is based on one of over 300 workshops and worksheets found in the eight books of the RevenueVsSales.com and TheFocusedSeller.com book series.

We’d love your help growing the list. Please share the newsletter with one person you think would benefit from it and ask them to sign up. Thank you!

To suggest workshops you’d like to read next, email [email protected]

Thanks for reading! Please share the subscribe link with 1 other person or your entire team, https://therevenueworkshop.beehiiv.com/subscribe.