Alex Gunnar@imalexgunnar
Playbooks
Playbook

Chief of Staff Hiring Playbook

How to hire a Miami-based Chief of Staff for OVO Talent

The retail/waitressing insight + age band + sourcing strategy that beats the Mina-shape unicorn search.

core
HiringTalent acquisitionFounder operations

Filter for the climb, not just the venue. The educator who got promoted is gold. The waitress still serving 3 years in is the warning.

Chief of Staff Hiring Playbook

The Doctrine

Filter for the climb, not just the venue. Hire single 25-29 Miami women who've been promoted in customer-facing roles, not stacked unicorn filters that produce another Mina rejection.

Locked 2026-05-10 after 3 weeks of iteration. The Mina rejection wasn't bad luck — it was a structurally wrong role spec. This playbook captures the role spec that actually works, the candidate archetypes that fit, and the sourcing strategy that ships in 2-3 weeks instead of 3 months.


The Role — Chief of Staff, OVO Talent

Title: Chief of Staff, OVO Talent (NOT "Brand Lead with equity in Brand Alex Inc.")

Location: Miami-based. No relocation REQUIRED but acceptable for the right candidate.

Cadence:

  • In-person 4-5 days/week when Alex is in Miami
  • Travels alongside Alex when he travels (NOT 24/7 lifestyle partner)
  • Business hours with founder-life flexibility (early mornings / occasional late nights / brand events)
  • Not the 10-week Europe summer block — Jaci handles that

Owns:

  • Alex's calendar, logistics, day-of execution
  • Talent close pipeline (sources/closes deals to OVO Talent + Academy)
  • On-camera presence in content during shoots/events
  • In-meeting presence at brand events, podcasts, partnerships
  • Vendor + agency coordination

Doesn't own:

  • Brand voice (Jaci)
  • Academy hosting (Jaci)
  • Outbound SDR (Welah/Joanna)
  • Long Europe summer block (Jaci)

Comp:

  • $5-8k/mo base
  • 10% commission on cash collected on deals she sources or closes
  • AmEx covered while traveling for work
  • Small content/ops bonus ($500/mo if hits KPIs)
  • Equity: Skip at hire. Revisit at month 12 if she's the one.

The Candidate Profile — Locked

Age: 25-29. Hard floor at 25 (avoids the 23-24 flake risk that killed Mina). 30+ is fine if exceptional but not the search target.

Marital status: Single (Alex's spec — travel/lifestyle compatibility).

Location: Miami metro (Brickell, Coral Gables, Doral, Wynwood, Miami Beach, South Beach) OR willing to relocate to Miami.

Background — any of these archetypes:

Tier 1 — Promoted retail at lifestyle/wellness brand

  • Alo Yoga (Aventura, Brickell, Lincoln Road, Wynwood stores)
  • Lululemon (Miami Design District, Aventura, Coral Gables)
  • Vuori (Coconut Grove)
  • Aerie / American Eagle Brand Ambassadors
  • SoulCycle / Equinox (instructor/manager track)

Promoted from sales associate → educator → community lead → store manager. The climb signal is non-negotiable.

Tier 2 — Upscale Miami service (promoted)

  • Major Food Group spots: Carbone Miami, ZZ's Club, Sadelle's, Contessa
  • Casa Tua (member's club)
  • Le Jardinier, L'Atelier de Joël Robuchon
  • The Surf Club (Four Seasons)
  • Komodo, Sexy Fish, Swan, Papi Steak (Groot brothers)
  • Soho Beach House members staff
  • Standard Spa restaurant + events

Promoted to lead server, events coordinator, GM, or moved to BOH ops. Plain waitress 3 years deep without promotion = warning, not signal.

Tier 3 — Hospitality with corporate ladder

  • Setai, Edition, 1 Hotel, Faena hotel concierge / events
  • Brand event hostessing → coordinator (F1, Art Basel, Formula 1)
  • Members clubs (Mr. C, ZZ's, Casa Tua) staff who climbed

Tier 4 — Ex-DTC brand corporate (the original archetype, kept as option)

  • Skims, Whoop, Celsius, Glossier, Aerie, Alo, Vuori, Hims, Athletic Greens, Red Bull
  • Past title: Brand / Marketing / PR / Account / Communications
  • Currently: Founder / Consultant / Strategist (escaped corporate)

Why retail/service Tiers 1-3 beat Tier 4 for THIS role

Skill / traitHow retail/waitressing trains it
Work ethic8-hour shifts, weekends, holidays. No-ego execution.
Customer service muscle100s of interactions/week. Rapport-building is reflex.
Sales repsEvery interaction is a micro-pitch.
Image-consciousAlo/Lulu literally hire on aesthetic + brand fit. Self-trained.
Charm under pressureRush hour, difficult customers, multi-tasking.
Real confidencePitching strangers daily builds it. Not corporate-faked.
Hungry to level upKnows the ceiling on retail/service. Motivated.
No corporate baggageField-trained, not process-trained.

The hidden gem: the lead educator at Alo or the promoted server at Carbone has been operating in higher-stakes situations than the marketing coordinator at Skims sitting in meetings. Just paid less and has no LinkedIn brand.


What to Avoid (Failure Modes)

ProfileWhy avoid
Age 23-24Mina-flake band. High agency at this age = stepping stone to own brand.
MarriedPer Alex's spec. (Married 28-35 was lower-risk but Alex declined.)
Has own creator brand with 10k+ followingIdentity = talent, not operator. Will leave to go solo in 9 months.
Plain waitress 3+ years no promotionNo operator signal. Just service muscle.
Actress/model with serving as fallbackOptimizing for own career, you're a stepping stone.
Corporate marketing manager STILL at the companyWon't take $45-96k base, entrenched.
Looking for "her own brand within the role"Mina pattern. Identity will compete with execution.
Wants to relocate from CA / NYCA/NY labor law disasters. Stick FL/TX/TN/AZ.
From abroad (Europe, etc.)Immigration wall — $20-30k legal + 12-24 months for work visa.

The Killer Interview Question

"What's your dream career arc 5 years from now?"

  • ✅ "Become VP/COO/operator behind a successful founder" / "I tried creator life and don't want it" / "I want to produce, not perform" → real candidate
  • ❌ "Have my own brand" / "Be a known creator" / "Launch a podcast" / "Have my own [thing]" → using you as a step

Ask this on call #1, before anything else. Saves 2 months of finding out the wrong way.


Other Interview Questions (Retail/Service Archetype)

  1. "Walk me through a hard customer interaction and how you handled it." — tests real-world execution
  2. "Why are you leaving retail/service?" — tests whether they've thought about the ceiling
  3. "What's the biggest thing you've taken ownership of outside your job description?" — tests for operator initiative
  4. "What was the last thing you proactively built or improved without being asked?" — tests for agency

Sourcing Strategy — 5 Channels

Channel 1 — Instagram geo-search (best for retail/service)

  • Search by location (Carbone Miami, Casa Tua, Alo Aventura, etc.)
  • Look at staff tagged in posts and check-ins
  • Filter: 25-29, single signal (no consistent partner posts), polished aesthetic, recent activity
  • 5 minutes per location, 50 candidates surfaced

Channel 2 — DM the brand stores directly

  • Hit Alo / Lulu / Vuori Miami stores in person on a "browsing" pretext
  • Observe educators, get business cards
  • DM the store account or manager: "Looking for an educator ready to level up into a brand role"
  • Most managers will forward — they want their staff to win

Channel 3 — Network referrals (highest quality, 0 cost)

  • Post on Alex's IG / Twitter: "hiring chief of staff at ovo. looking for ex-alo/lulu educator or carbone-tier service operator ready to level up. 25-29, miami-based. dm or refer."
  • Your existing network has 50+ people who know exactly this profile
  • Reply rate 30-40%, quality 5x cold outreach

Channel 4 — LinkedIn boolean (best for ex-corporate Tier 4)

women, current location: Miami / Miami Beach / Coral Gables / Brickell / Doral / Wynwood
graduation year: 2017-2021 (puts at 25-29)

EITHER:
  past company: (Alo Yoga OR Lululemon OR Vuori OR Aerie OR SoulCycle OR Equinox)
  past title: (Educator OR "Lead Educator" OR "Community Lead" OR "Store Manager" OR Ambassador)
OR:
  past company: (Skims OR Whoop OR Celsius OR Glossier OR Hims OR Athletic Greens OR Red Bull)
  past title: (Brand OR Marketing OR PR OR Account OR Communications)

CURRENT status: NOT still at the past company (escaped signal)

Channel 5 — Cross-reference Instagram (verify aesthetic + active)

For each LinkedIn match, find Instagram. Confirm:

  • Active in last 30 days
  • Polished aesthetic (camera-ready)
  • Lifestyle/professional content (not pure influencer)
  • Geo-tagged posts in Miami
  • No "in a relationship" / engagement posts (single signal verification)

The DM Pitch (Use This)

hey [name], saw your work at [brand] and your recent [specific
post reference]. quick: i'm hiring a chief of staff at ovo
talent (creator agency, miami based). looking for someone w/
your background — ex-[brand] or upscale miami service, polished,
ready for an operator seat.

miami-based, no relocation needed, travel with me sometimes.
$5-8k base + 10% commission + amex.

15 min call this week if interesting? [calendly link]

The "[specific thing]" line is non-negotiable. Generic DMs get ignored. 30 seconds on her grid → write one specific reference → reply rate jumps from 10% to 40%.


The Trial Structure

Don't sign full contract on day 1. Run a 30-day Miami trial first:

  • Days 1-7: Shadow Alex, learn the systems, meet the team (Welah, Joanna, Jaci, Patricia, Lucas)
  • Days 8-21: Take ownership of one closed function (calendar OR Talent close OR brand events). Show execution.
  • Days 22-30: Mutual evaluation. Either side can walk no questions asked.
  • Day 31: Sign full contract OR clean exit with thank-you bonus.

This was the Mina lesson — "fly Sunday and live with you forever" is too much commitment too fast. 30-day trial de-risks both sides.


The 5-Year Outcome

The right hire compounds. By Year 3:

  • She's running Talent close pipeline at $X MRR
  • She knows your business deeply enough to make founder-level decisions in your absence
  • She's grown into Director of Operations or VP-level seat
  • Her comp has scaled to $150-200k + meaningful equity (Year 2 grant)
  • She's the first call when something breaks

The wrong hire churns at month 6-12 and you start over. Every churn costs ~$30-50k in salary + onboarding + opportunity cost.

Hire ruthlessly for the right one. Take the extra 2 weeks if needed.


Mentor Lessons (From the 3-Week Search Iteration)

  1. Stop solution-shopping for the same archetype. "Find Mina v2 with different filter words" doesn't work. The candidate type isn't the problem — the role spec is.
  2. In-person + travel-when-traveling > 24/7 lifestyle partner. Option A is hireable in 30 days. Option B is the Mina trap.
  3. Don't stack unicorn filters. Picking 8 filters (age + single + Miami + ex-DTC + sorority + travel + camera-ready + escaped corporate) creates a 50-person nationwide pool. Pick 3-4 critical filters and accept variance on the rest.
  4. The dream-arc question filters 80% of risk. Ask it on call #1.
  5. The retail/service climb signal beats the corporate resume signal at Chief of Staff level. Field-trained > process-trained for someone who'll execute alongside a founder.
  6. Skip equity at hire. Revisit at month 12. Equity at hire makes the role feel transactional. Cash + commission proves the relationship before locking the cap table.
  7. The 30-day trial is non-negotiable. Both sides need an exit ramp. Mina pulled out partly because no exit was visible upfront.

Cross-References

  • Memory: feedback_alex_ceo_operating_system.md (the umbrella for team direction)
  • Memory: feedback_softness_is_contextual.md (CEO mode applies to this hire)
  • Memory: project_mina_mueller_hire.md (the original failed search — what we learned)
  • Memory: project_active_team_payroll.md (existing team this hire supplements)
  • Playbook: ceo-operating-system.md (how to direct her once hired)