Growth required more operator time.
A full-time employee was manually managing a strategically important pipeline that leadership could not clearly see.
Demand was growing faster than the operation behind it.
For a marketplace, a win on one side of the business can become a constraint on the other.
Storetasker was attracting clients through cold email and paid traffic. To serve that demand, the company also needed to find, assess, and onboard more high-quality Shopify freelancers. What had once been secondary to customer acquisition was now part of the critical path to growth.
A dedicated employee was spending most of their time manually managing applications and follow-up. Data lived across disconnected sources, duplicate records distorted the picture, and the team had no reliable view of conversion or friction at each stage.
The Fractional COO concern
The question was not simply “How do we automate onboarding?” It was “How do we keep a strategic growth channel viable without adding the same amount of management work?”
The team did not need more effort. It needed a visible operating system.
I started by shadowing the people closest to the work. That exposed two immediate problems: poor data hygiene made the real state of the pipeline difficult to understand, and repetitive tasks were consuming attention that should have gone to judgment and improvement.
Before adding automation, the operation needed a clean model of the work: one source of truth, clear stages, meaningful conversion points, and an explicit next action for each person in the pipeline.
What leadership needed to be able to see
- How many freelancers were at each stage of the journey
- Where qualified applicants were slowing down or dropping out
- Which acquisition channels produced the strongest candidates
- Where a person’s judgment was valuable—and where the system could move the work
Clean the signal, clarify the work, then automate the drag.
We deduplicated applications and combined the scattered data into one clean database. With a reliable picture of the funnel, we broke the freelancer journey into clear stages and built dashboards that showed the queue, conversion, and next action at each point.
Then we automated the repeatable work: emails at the right moments, reviews where the criteria supported them, reminders that kept candidates moving, and clear visibility into the cases that still needed human attention.
The new visibility also improved strategy. Storetasker could concentrate on its strongest acquisition channels and identify the traits shared by successful freelancers earlier in the process.
Why this required operating ownership
The value did not come from one automation. It came from connecting acquisition strategy, the team’s day-to-day work, funnel data, and the technology carrying the process.
The result
A growth bottleneck became an operating advantage.
In four weeks, Storetasker had a larger pipeline, a clearer management picture, and an operation that demanded far less manual attention.
2×freelancer pipeline in four weeks
~75%less time spent managing the supply side
1clean view of the funnel and the metrics that mattered
“Jackson’s secret power is his ability to automate nearly everything he touches. He consistently got callouts in our quarterly board meetings. If I could, I would clone Jackson 100 times over.”
Sam WilcoxonCEO & Co-Founder, Storetasker
