How to Hire the Right Operations Partner for Your Small Business

Here's the revised version:

You're Not Hiring Wrong. You're Looking at the Wrong Things.

Ashley Connell had already burned herself out before she figured out what was actually missing.

She started Prowess Project to give women flexible careers. She had the vision, the relationships, the drive — and zero systems. "I immediately stalled," she said. "I am the sales, the marketing, the relationships person. I know nothing about systems, about data, nothing."

Then she met Leah. Leah became her operations person, and later her COO. Within months, other CEOs were asking Ashley how she'd grown so fast. Her answer: "It's Leah." Their response: "I need a Leah."

That's how Prowess Project became what it is now — a training and matching program that places operations partners with small business owners. They've built an algorithm that evaluates hundreds of behavioral and communication indicators. They match people in four business days. Ninety-four percent of placements stick. The other 6% get a rematch.

The algorithm deliberately ignores most of what traditional hiring asks for.

Sam put it plainly mid-episode: "Knowing if this person has worked in HubSpot before is... who cares?" Ashley didn't push back. The indicators that actually predict a working relationship aren't on any resume — work style, communication approach, emotional intelligence, how someone handles feedback, gives feedback, and functions next to someone who operates completely differently. "You need a partner who is compatible," Ashley said. "Not same compatible."

The algorithm even surfaced one match where the CEO called Ashley immediately after seeing the candidates to pull one from the pool. Reason: they'd dated.

Ashley's take: "If this does not work out as CEO-ops matching, this can absolutely work out for dating."

The Niching Problem She Had to Solve Twice

Before Prowess became what it is now, it was trying to be the LinkedIn for moms. Any role, any skill set — if she was a mom who needed flexible work, Prowess had her. That didn't scale. So they narrowed to operations only, for small professional services businesses.

They thought that was enough. It wasn't.

"Trying to market to someone who runs a recruiting business is wildly different than trying to attract someone who has an accounting business," Ashley said. Last fall they made the call again: all outbound would target accounting firm owners, tax strategists, and fractional CFOs. Not as a filter — as a magnet. Non-accounting businesses can still work with Prowess. Prowess just stopped chasing them.

Six and a half years in. That's when the second light bulb hit.

Sam caught it in real time: "The light bulb moments don't always come overnight or as easy as we want them to."

Ashley didn't dress it up. "You never really know. We are testing this for 365 days... We could crash and burn."

That's the part founders tend to skip over when they tell their own stories. The experiments that haven't been proven yet. The bets that are still open. Ashley left it open.

What Your Ops Person Is Actually There to Do

Here's where a lot of founders get into trouble — they bring someone in without being able to answer the question "what are they doing each week?" Expectations get muddy fast, and the relationship starts breaking down before it ever had a real chance.

Ashley's ops partners enter every engagement with a four-step framework: audit the business first, then build and wrap tech around the existing systems and processes, set up project and task management, and build a dashboard so the CEO has the right data to make decisions. After the audit, the ops partner delivers a 90-day project plan broken into two-week sprints. The CEO knows what's getting done and when. The ops partner knows what they're accountable for.

"As soon as we got really clear that these are the four things that our ops partners are going to deliver, then it made everything easier," Ashley said. Sales conversations got cleaner. Expectations landed. It didn't require a new tool or a bigger budget — it required getting specific about the scope.

Two other things worth pulling from that part of the conversation:

Communicate behaviors, not outcomes. "They cannot control the sale. They can control how many people they call." If you're telling someone you want results without telling them what actions to take, that's not delegation — that's a wish.

Don't automate a broken process. "All that happens when you wrap technology around it is you speed up whatever that process is. So if the process is broken, you are going to speed up a bunch of broken inputs." AI is not the fix. Fixing the process first is the fix. Then you can talk about AI.

Sam's been saying a version of the second one for a while. Nice to hear it land the same way from someone coming at it from a completely different angle.

Before You Hire Anyone

Ashley's starting point for any founder who thinks they might need an ops partner: do a two-week time study. Every 15 minutes, write down what you just did.

"You will be shocked at how much time you waste, how much time you could delegate to someone else, how much time you are doing stuff you hate doing."

From there you have real data — not gut feelings, not assumptions — about what to cut, what to hand off, and where you actually need to be spending your time.

Leah sends Ashley a Slack at 7 AM on time study Mondays to make sure it happens. That's the system. It's not glamorous. It works.

If you've been putting off figuring out what kind of help you actually need, that's where to start. Two weeks, 15-minute intervals, no shortcuts. Go do the thing.

Ashley Connell is the CEO of Prowess Project, a training and matching platform for operations professionals and the small businesses that need them. Find her at prowessproject.co.

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