Building a Sales Ops Role in a Mid-Size Travel Agency
Six months before Maya hired Sales Ops, she would have told you she didn't need Sales Ops. She was the founder, she'd built the pipeline herself, and she could pull any number out of the CRM in ten minutes. By the time her agency hit twenty-five agents that ten minutes had turned into half a Friday, and the numbers stopped agreeing with themselves.
This is the story of the role she finally drew on the org chart, who she hired to fill it, and what changed in the ninety days after.
The Friday the Math Disagreed
She was reconciling commissions for the month. Two CRMs (the old one she hadn't fully migrated off, and the new one), one fulfilment spreadsheet, and a column in finance's system she'd been told was the source of truth. The three numbers came out within a few hundred dollars of each other, which sounds close until three agents are waiting on a payout and the smallest discrepancy reads like an accusation.
She kept the agency's books honest by working until 9pm and rounding up where the math was unclear. That weekend she stopped opening Excel and opened her org chart instead.
What Sales Ops Actually Means at Twenty-Five Agents
Sales Ops at this scale isn't a Salesforce admin job and it isn't a junior data analyst job. It's five things that, until now, had been quietly falling on Maya in slivers across every week:
- Pipeline hygiene, making sure the stages, owners, and amounts in the CRM actually match reality.
- Commission calculation, every cycle, in time, with math the agents trust without asking twice.
- Weekly forecast, a number leadership can plan with, not a vibe.
- Dashboards, the three or four metrics the agency actually steers by, refreshed without anyone begging for them.
- Sales-to-fulfilment friction, the person who notices when a closed deal is sitting in a queue and pokes the right shoulder.
Five jobs in one head. Maya had been doing four of them badly and the fifth (number five) not at all.
Hire or Outsource
She called a peer who'd run a thirty-agent agency two years ahead of her. His advice was the kind of advice that sounds like it was cheaper to take than to ignore. Don't outsource Sales Ops until you've had it in-house for a year. You can't write a good brief for a fractional consultant when you don't yet know which part of the job hurts the most. You need a hire who can sit at your desk for ninety days and tell you where the friction actually lives.
She'd been close to signing a fractional contract that week. She didn't.
The Job Description She Actually Wrote
Three asks, no more.
Two-plus years in sales ops or revops at a similar-sized company. Comfortable in CRM admin and in a spreadsheet, because at this stage of agency you don't get to pick one or the other. And, the line that filtered out half her applicants, has at one point owned commission calculation end-to-end. The job is mostly about agents trusting numbers. The clearest signal a candidate can give is that they've already done the work where money was on the line and the math had to be right.
She left out the things she'd seen in other postings: SQL skills, Tableau certifications, a four-year degree. None of them were going to determine whether the next Friday went better than the last.
First Thirty Days: Forensics
The hire's first thirty days were forensics. Where did the commission numbers actually come from? Which agents had pipeline that didn't match what they were saying in standup? What had been broken so long that nobody flagged it anymore?
Maya's instinct was to fix things alongside her. She held back. The point of the first month was for the new person to find what Maya had stopped seeing, the things you stop noticing when you've worked around them for two years. By the end of week four, the hire walked Maya through eleven concrete things they'd found, six of which Maya hadn't known about.
Days Thirty-One to Sixty: Rebuild the Commission Loop
The biggest thing the forensics surfaced was that the commission process had been built for five agents and patched four times to fit twenty-five. The hire spent month two rebuilding it from the source data up. New report definitions in the CRM, a single source-of-truth table, a payout draft that finance could review without re-deriving anything, and a dispute path that didn't end in Maya's inbox.
The Friday that month closed, commission ran in forty minutes. Maya was on a sales call.
Days Sixty-One to Ninety: Telling Maya Things She Didn't Know
By month three the forensics phase had paid for itself. The hire walked into Maya's Tuesday one-on-one with three observations Maya hadn't seen.
Two of her best agents were sandbagging because the tier structure penalized predictable months. One product line had a 38% close rate at the inquiry stage but only 12% at the proposal stage, which meant something was breaking in pricing, not in lead quality. And the agency's average response SLA had quietly drifted from two hours to four-and-a-half over the previous quarter, with no single moment of failure to explain it.
That third one led to the playbook on multi-department handoffs. The first led to the tiered-commission rebuild.
How You Know It's Working
The signal isn't a clean dashboard. It's the slow disappearance of certain questions from Maya's day. Agents stop asking her about commission timing. The Friday forecast gets filed without her review. Two hours reappear on her Tuesdays that used to be spent in spreadsheets.
The clearest test, though, is what happens when she takes a week off. Before the hire, she came back to a backlog. After, she came back to a one-page memo of what had moved and what was waiting on her decision. The agency had run.
When the Second Sales Ops Hire Comes
Roughly at fifty agents. The role splits along a natural seam: the first hire becomes a Sales Ops Lead who owns analytics, dashboards, and the weekly forecast. The second hire owns the quote-to-cash loop end to end, including commissions and the handoff to fulfilment. The mistake at this point is asking one person to keep doing both, which is how Maya ended up in the spreadsheet on that Friday in the first place.
If you're already past thirty agents and still don't have anyone in the role, you're not early. You're late. The cost isn't visible the way a missed sales target is, but it's there in every Friday that runs longer than it should.
Further Reading
- Multi-Department Handoffs: Sales, Fulfilment, Service. What the new Sales Ops hire surfaced first.
- Tiered Commissions That Retain Your Top Producers. The next thing to rebuild after the calculation loop is clean.
- Hiring Managers vs Promoting Your Best Producers. The other foundational hiring decision at this stage.
- Lead response time. Why a four-hour SLA quietly costs more than a two-hour one.
Growth Partner
On this page
- The Friday the Math Disagreed
- What Sales Ops Actually Means at Twenty-Five Agents
- Hire or Outsource
- The Job Description She Actually Wrote
- First Thirty Days: Forensics
- Days Thirty-One to Sixty: Rebuild the Commission Loop
- Days Sixty-One to Ninety: Telling Maya Things She Didn't Know
- How You Know It's Working
- When the Second Sales Ops Hire Comes
- Further Reading