The first version
Tatum joined Sable AI shortly after the company's Series A. The product was working. The team was small enough to fit in a single room: a handful of engineers, two designers, a head of growth, and a founder. There was no chief of staff. There was no operations head. Tatum was hired to be both, with the title chief of staff and the understanding that the work would shape itself around what the company needed.
The work, for the first nine months, was the work of a thirty-person company. She owned the calendar, the standing meetings, the candidate experience for the first wave of senior hires, the off-sites, the all-hands cadence, the founder's external schedule, the relationship with the board, the contracts she could review without legal, and the contracts she'd flag to outside counsel. She built each of those things from nothing.
Then the company closed an $80M Series B. Ninety days later, Sable was sixty people, growing at five new hires a week, with a founder whose travel had tripled and a calendar that no longer fit inside a single chief of staff's bandwidth.
"Everything I built at thirty people is the first version. At sixty people, the first version is the constraint. That's the part nobody warns you about."
What breaks first
The standing meetings break first. The all-hands that worked at thirty people doesn't work at sixty. The product review that worked at four engineers doesn't work at sixteen. The candidate experience Tatum had built — a four-touch process with a personal note from the founder for every offer — does not scale to a hundred and forty interviews a week.
"Every system has a number," Tatum says. "Below that number, the system is the answer. Above that number, the system is the problem. At thirty people, my four-touch hiring loop was the best thing about working at Sable. At sixty people, the same loop is the bottleneck on the company shipping its next model."
The second version
Tatum is now ninety days into building the second version of her job. She has hired an executive assistant — her first direct report. She has architected a chief-of-staff function with two clear surfaces: the founder's office (her), and the operating cadence of the company (an incoming head of operations). She has redesigned every system she built in the first nine months. She has fired three vendors and added five. She has rewritten the all-hands format. She has rewritten the offer letter.
"Ninety days post-B is its own job," she says. "It's the job of de-bottlenecking everything you built in the first version of the job, in real time, while the founder is on the road every other week."
"My job changed without my title changing. I had to notice it had changed before anyone else did. That's the load-bearing skill."
What she'd outsource
"The candidate experience at scale," Tatum says. "There is a vendor for sourcing. There is a vendor for scheduling. There is no vendor for the experience — the part of the candidate process that says working at Sable feels like this. That's still a hand-built thing. I want a vendor for that. I don't think it should exist, but I want it."
Topics covered
- The chief-of-staff role at a thirty-person company versus a sixty-person company
- The systems that break first when headcount doubles
- Rebuilding the function in ninety days while the founder is on the road
- The load-bearing skill of noticing the job has changed