Helping businesses‑of‑one make confident financial decisions.
I sell financial software to the people who run the business, mostly over video, in short cycles. I’m applying for Collective’s Account Executive role.
Owner calls are rarely about features.
- What is eating my time?
- What am I paying that I don’t fully understand?
- Am I set up right for what I’m earning now?
- Who can I trust to handle this?
A business-of-one is usually a skilled professional who never set out to become their own accountant. Those four questions are what they’re really asking, whatever they say first.
That’s what makes Collective interesting to me. The job isn’t to sell bookkeeping, payroll, and tax filing as separate line items. It’s to help an owner see how those pieces fit together, and whether a different setup would give them back time and more of what they earn.
How I’d run a member call
Discover first
Learn the business before the product: what they do, how they earn, how they’re set up today (sole proprietor, LLC, or S Corp), who handles the books and payroll, and what last tax season felt like.
Translate
Turn entity, payroll, and bookkeeping concepts into plain trade-offs the owner can weigh. At Intuit I did this with owners and their bookkeepers on accounting, payroll, and tax-season work; as an ISO I did it with rates and fees against the owner’s margin.
Earn the decision
Fast cycles only work when the buyer feels understood. At Sales Flow I ran back-to-back virtual closing calls that closed same day or next day, and at Intuit my wins closed on the same call.
Follow through
Phone, email, text, or video, whichever keeps the conversation moving without making the owner feel chased. Text was a core channel in building relationships with 100+ McDonald’s franchise operators.
Hand off cleanly
Set expectations on the call that Member Services can deliver on, so a new member’s first month matches what they said yes to.
Track record
~20 closes a month at a ~25% close rate, on deals that closed same day or next day
Sales Flow Marketing, 2020–202338% win rate selling QuickBooks accounting, payroll, and payments to small and mid-sized businesses
Intuit, 2024–2025Grew a payroll and compliance book across multi-location McDonald’s franchise operators over ~18 months, taking ARR from ~$500K to $1M+
Employer Benefit Systems, 2015–2019Built a merchant-processing book from zero while owning and running the business
Independent ISO of Chase Paymentech, 2008–2012Built a library of winning calls for team coaching after the top-performer review, and proposed making it permanent
Sales Flow Marketing