How to Create a Seamless Hiring Workflow

Most hiring advice is garbage. At Winc, I was responsible for hiring dozens of key roles, from General Managers of our key brands, to heads of departments like performance marketing, retention, data, and engineering. I made some A+ hires, but also made some terrible ones. Here’s how I would structure a hiring process if I had to redo it all again. 1. Ditch the corporate-speak job posting and source 10-20 quality candidates via LinkedIn The best candidates are not applying to jobs. You spend a ton of time drafting a job post, and even more time combing through unqualified or low-intent resumes. Instead, I’d get LinkedIn Sales Navigator and look for rising talent that is 1 level below the role you’re trying to hire for with experience at similarly sized (or slightly larger) companies . For example, if you’re hiring for a Director of Retention, reach out to Senior Retention Managers. This is similar to the approach a recruiter may take and will save you $25K+ in commissions. 2. Ask detailed, personalized questions in the interview Forget vague, templated questions like “Tell me your 3 biggest strengths and weaknesses.” Those questions are lazy, and most candidates are trained to respond to them in a scripted way. Instead, ask detailed questions about their accomplishments on their resume. “You said you increased revenue by 50%, tell me about how you did that and what role others played in that process?” 3. Grill them on current trends in their area of expertise Candidates that are passionate about what they do keep up with trends in their domain. For example, if you’re hiring an SEO manager, ask about the current landscape of AI-driven content and how that currently shapes Google’s organic ranking strategy. Listen for an understanding of nuance and the ability to hear and weigh an opposing standpoint. 4. Spend time with them in a non-interview setting You’ll learn much more about someone over coffee, drinks, or dinner in-person than you would behind a computer screen. Look out for characteristics like graciousness (when you pay for the meal), politeness (to service staff), decisiveness (when ordering), etc. See if they’re someone you’d want to spend most of your time with. 5. Give them a case study to complete Getting sample work is a great way to gauge whether or not that candidate’s work product exceeds your expectations. This shouldn’t have to be a paid engagement for the most part. Tell them not to spend more than 30 mins - 1hr on it. If they actually care, they’ll spend more time and it’ll show in the output. 6. Hire them fractionally first Most people can spare 5-10 hours for a couple weeks to “test the waters” at a new job. Work with them for a bit on a fractional basis to see how they integrate with your team. By hiring fractionally first, you’ll get a great read on them and they’ll be able to gauge whether or not your company is one they want to be at long term.

Résumés are dead signal. And most companies are still using them to make multi-hundred-thousand-dollar hiring decisions. Many HR functions are facilitating a dysfunctional process and not a critical business enablement function that gives leverage to the business. (Also highly frustrating to job seekers spending hours on resumes, applications, and interviews.) If your recruiting process starts with a résumé review and ends with a generic job description, you’re optimizing for polish—not performance. Here’s what high-growth, high-trust hiring actually looks like: 1. Hire from work, not words. Résumés are marketing copy. Ask: “What did you build that still works without you?” Have them walk you through it. A deck. A dashboard. A system. The best operators speak in outcomes. Everyone else describes process. 2. Prioritize ownership over optics. “Led,” “managed,” “oversaw”—those are spectator words. Ask: “What decision did you make—and what tradeoffs did you weigh?” Use this framework: What was the situation? What was your call? What happened next? You’ll know if they owned it—or just had a front-row seat. 3. Screen for judgment, not perfection. You’re not hiring someone who’s always right. You’re hiring someone who gets smarter with every rep. Ask: “What’s a decision you’d revisit now with new information?” Judgment compounds faster than skills. Look for signal that they’ve updated their playbook. 4. Run performance-based interviews. Would you greenlight a $300K contract based on a résumé and three Zoom calls? Then stop hiring that way. Create a scoped, role-relevant project. Debrief it live. You’re not testing polish—you’re testing how they think under pressure and with context. 5. Stop mistaking pedigree for potential. A Stanford degree or FAANG stint is just context, not signal. Ask: “What did you do that others around you weren’t doing?” Look for stretch, creativity, and earned scope. 10x people don’t always come from the obvious places. 6. Ditch culture fit. Define behavior. “Culture fit” is often a proxy for “feels familiar.” And that’s how you build sameness, not scale. Ask yourself: “What are the behaviors our best people consistently demonstrate?” Interview for those. Not vibes. Not style. 7. Design the org first. Then hire. Too many job descriptions are written after someone quits. That’s backfilling, not architecting. Ask: “What friction does this role unblock? What velocity does it add?” You can’t hire for leverage if you don’t map where you need it. 8. Hire for trajectory—not title. Title is a lagging indicator. Trajectory is a leading one. Ask: “Where were you two years ago—and what’s changed since?” Look for acceleration. People who scale themselves can scale your company. You don’t build a generational company by playing it safe. You build it by designing a hiring system that finds slope, judgment, and ownership—and rewards it.

Most hiring teams waste 70% of their time on the wrong candidates. Here’s how the best operators cut that down: 1) Define “must-haves” in writing. Not 20 bullet points. Three non-negotiables. If a candidate doesn’t meet them, don’t interview. 2) Move the work sample forward. Stop waiting until the final round. A 30-min project upfront saves you hours of interviews with the wrong people. 3) Track candidate velocity. If your process takes 30+ days, you’re losing A-players. Build dashboards that show where candidates stall — and cut bottlenecks. 4) Scorecards > gut feel. Every interviewer rates skills against pre-set criteria. No “I just liked them.” No bias. 5) Onboard before you celebrate. The best hires fail when onboarding fails. Treat the first 30 days as part of the hiring process, not the end of it. Here’s the truth: Hiring isn’t about picking talent. It’s about building the system that attracts, closes, and ramps them.

I recently stumbled upon Geoff Smart and Randy Street's hiring methodology… Here’s what I learned: The true cost of a hiring mistake? 15x the person's salary. Yet most managers: • Rush the process • Rely on gut feeling • Ask ineffective questions • Skip thorough reference checks The "A Method" that transformed our hiring process: 1. Create a scorecard first Don't just list requirements - define the exact outcomes this person needs to deliver. 2. Source strategically The best candidates come through referrals. Incentivize your team to connect you with top talent. 3. Conduct four progressive interviews Dig deeper with each conversation. Push for detailed examples, not hypothetical answers. 4. Check references properly Have candidates notify their references in advance. Listen for what isn't said - lukewarm praise speaks volumes. Remember: A-players deliver exponentially better results than B-players. Hiring isn't about filling seats… It's about finding people who can drive real outcomes.

At the end of last year, Revv was 20 people. Now we're a team of more than 70! Here's how Jessica Plummer (our head of talent) and I tripled our headcount in 6 months without losing our DNA: 1. Make hiring a repeatable motion, not a gut feeling We build clear 30-60-90 day expectations, role-specific scorecards, salary bands, compensation frameworks, and equity benchmarks—all tailored to Revv and paired with each hiring manager. Every team gets individualized onboarding because cookie-cutter *never* works. 2. Trust your people, but quarterback the big hires I delegate IC hiring through final rounds—I only jump in before we extend offers. But for executives, I'm quarterbacking every single conversation. Alignment with founder-values is non-negotiable at the top. 3. Use systems (and AI in this age) to scale your decision-making We've built multiple systems to scale hiring decisions—HRIS integrations, role-specific processes, and an AI workflow that takes meeting notes and feeds them to an LLM trained on my scorecards with examples of how I map conversations to benchmarks. It helps me evaluate candidates apples-to-apples and saves hours of manual assessment. 4. Build structure around values, not just skills Every single person is a percentage addition to your culture. Screen for energy and alignment first, credentials second. Hiring at scale is a systems game. Master the system, and you'll never compromise on quality!