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 discovery 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 discovery call, 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

Built by an operator who rebuilt his own life through the same work — now scaling it.

ChiefDesk was founded by Yusef-Andre Wiley, who scaled a reentry and housing nonprofit from $4M to $9.5M while managing government contracts with LA County, CDCR, and multiple philanthropic funders. The platform is the backend infrastructure he wishes had existed while he was running lean — now packaged for any leader running lean.

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 contact@ywconsultants.com.

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 discovery call.

Email your resumeRead the founder story →

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.