What the work covers
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Go-to-market
How the company sells: pricing and packaging, the sales motion, and what each dollar of acquisition cost actually returns.
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Org design and leadership
Who does what, which roles are missing, and which are there because of history. Hiring plans that match the revenue plan.
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Reporting and operating cadence
Numbers the leadership team sees weekly, board reporting that holds up, and the meeting rhythm that makes decisions stick.
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Retention and unit economics
Why customers stay or leave, what each one is worth, and the renewal and collections work that follows from the answer.
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Cost structure and cash
Where money goes, what it buys, and how to take spend out without breaking the parts of the business that are working.
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AI and automation in the operation
Where software should absorb manual work, and where it adds noise. The systems get built, not just recommended.
How engagements run
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Fractional
A standing few days a month as the operating leader, with the leadership cadence and reporting to match.
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Interim
Full-time in the seat through a transition: a departure, an integration after a close, or a turn in the plan.
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Focused project
One question answered and fixed, such as the go-to-market model, the reporting stack, or the cost base.
Why an operator
This work is led by someone who has done the job, not advised on it. Bill Kindler co-founded Schoology, a K-12 software company acquired by PowerSchool, and served as its executive vice president through the exit. He was most recently chief operating officer at Gipper, where he rebuilt go-to-market and the cost structure of the business.
The difference in practice: recommendations come with the systems that carry them out, because the same person builds both. More about Bill.
Contact
Describe the work you have in mind, and we will tell you how we would approach it.
hello@outermost.us