We’re hiring

Independent closer & virtual assistant.

Commission-only · Remote · Flexible schedule

Help small teams and nonprofit operators discover the backend infrastructure built by an operator who needed it himself — and earn commission on every deal you close.

The role

Three areas. Pick the one you’re sharpest in — or cover all three.

Sales
Close prospects onto existing tiers
Run demo calls, qualify fit, and close prospects onto one of the four existing ChiefDesk plans — Starter, Growth, Nonprofit Pro, or Executive. The pitch and the product are already proven; your job is to match the right buyer to the right tier.
Relationships
Client outreach & after-sale support
Stay close to the buyers you bring on. Run check-ins, surface blockers, and feed onboarding observations back to the founder so the next cohort closes faster.
Operations
General VA support for the founder
Inbox triage, calendar scheduling, and document prep — the operator work that keeps the founder available for the calls only a founder can take.

Compensation

Paid when deals close.

No base salary. This engagement is commission-only — you earn on closed deals, not for time on the clock. Commission rates are tiered to the plan you close (Starter, Growth, Nonprofit Pro, or Executive), so a single Executive close pays several times what a Starter close does.

Exact tier rates are shared on the demo, after we’ve both seen whether the fit is right. If you’re early-stage in sales and willing to ramp, a reduced starting rate may be available while you build pipeline.

Who this fits

We hire for three things.

  • Independent contractors only.

    You operate as your own 1099 entity. We do not offer W-2 employment, benefits, or a base salary through this role.

  • Comfortable in a remote, async environment.

    Most coordination happens over email, Loom, and shared docs. You set your own hours; we care about outcomes, not punch cards.

  • Prior sales, recruiting, or VA experience is a plus.

    A track record of closing, sourcing talent, or running an executive’s backend reads well — but a sharp first-time closer with the right temperament is also the right fit.

The company, briefly

The founder's source-grounded background.

Yusef Wiley is the founder profiled here. Yusef Wiley is the Founder and Principal of YW Consultants and the Founder of Timelist Group. He grew a California reentry and housing organization from a $4M to a $9.5M budget. He advises government agencies, nonprofits, and community organizations on government contracts, program design, and leadership. He served as a Commissioner on the Union City Human Relations Commission and on Alameda County reentry panels and advisory boards. He authored If I Knew Then and What I Know Now, is a certified John Maxwell Team trainer and coach, and is a keynote speaker for universities, corporations, government, and correctional agencies.

That’s why this role exists. We’re hiring the people who can carry that mission into the conversations we can’t be in ourselves — closers who care about the buyer matching the right tier, not just the deal closing.

How to apply

Send your resume to chiefdesk-2@polsia.app.

Attach your resume (PDF preferred). In the body, include one short paragraph on why you’d close well — the rest we’ll cover on a 20-minute demo.

Subject line pre-fills to “Resume — Closer / Virtual Assistant Role”. We read every email.

Equal-opportunity independent-contractor engagement. Not a W-2 position.

Open to US and international contractors. Decisions based on fit, not on geography, school, or résumé pedigree.