People Operations Director

Why Shiftsmart

We’re building the Amazon of labor. We’re a labor platform pairing end-to-end workforce management technology with a rapidly growing global network of 5M flexible workers to create scalable labor solutions for the largest companies in the world, like Circle K, Pepsi, Dollar General, Starbucks and more. Our unique business model fractionalizes jobs down to shifts and makes it easy for workers to work across multiple companies through a digital marketplace. We’re one of the fastest-growing startups in the country. We’ve grown 2-3x each year since we started and raised $120M+ from top-tier investors including D1 Capital & Imaginary Ventures…and we’re only getting started.

Our mission is to build the world’s leading platform for hourly workers and enterprises enabling flexibility, choice, and upward social mobility.

• Join a rocketship. This is a unique opportunity to join the ground floor of a rapidly scaling business that is changing the way hourly labor works and capturing a $2 trillion dollar opportunity in the US alone.

• Ownership + impact. Join a team that is challenging and supporting one another to build a great business and create flexibility, choice, and upward social mobility for workers everywhere.

• Captain your career path. Enjoy accelerated learning and growth working with a world-class team from top tech companies (e.g. Uber, Airbnb, Google, Amazon), business schools (e.g. HBS, GSB, Wharton), and professional services (e.g. Bain, BCG, Goldman).

• Become a world-class executor. We believe that #ExecutionIsBinary, and are dedicated to helping you master that skill for life here and beyond.

Team Mission:

The mission of the People team is to make Shiftsmart the place where the best talent in the market chooses to build their career, and does their best work once they're here. That means finding and hiring people who raise our talent density, getting them productive and embedded in our ways of working fast, and building the systems (performance management, career growth, feedback) that keep our best people learning, growing, and staying. As Shiftsmart scales headcount, this leader will be responsible for building the people infrastructure including, recruiting capability, onboarding, and performance/retention systems that help us hire and retain a workforce that matches the ambition of the business, without sacrificing our talent bar or our culture.

This role is based in New York City (HQ) with typically 4+ days per week in the office.

Outcomes:

This leader owns three outcomes end to end: (1) the quality and speed of who we hire, (2) how successfully new hires ramp into Shiftsmart's ways of working, and (3) whether our best people grow and stay. They lead the recruiting team directly and act as the architect of the systems — interviewer training, onboarding programs, performance review cycles — that make hiring and retention repeatable rather than dependent on any one person's instincts. Like all managers at Shiftsmart, they operate as a player-coach: leading a team as leverage, while staying close enough to the data and the day-to-day to personally solve the biggest problems when needed. This person will work cross functionally to drive outcomes partnering closely with hiring managers and functional leaders across the company.

Responsibilities will include:

• Own talent acquisition end to end. Lead and develop the recruiting team, own hiring funnel metrics (time-to-fill, quality of hire, offer-accept rate) across the business, and be accountable when they improve or slip.

• Raise our talent bar. Design and run interviewer training that improves how the company assesses candidates — structured interview kits, calibrated scorecards, debrief practices — so we continue to raise the bar across interviewers and teams.

• Build onboarding that sticks. Develop and continuously improve onboarding materials and programs that get new hires productive, fast, and fluent in Shiftsmart's Operating Principles, tools, and ways of working — measured by early-tenure performance and retention.

• Run performance management. Own ongoing improvement and execution of performance review cycles (goal-setting, calibration, ratings, feedback) that reward performance and drive development in a way that’s clear, simple and easy to understand.

• Drive retention as a system, not a reaction. Identify where and why we lose good people, and build the programs (career pathing, manager effectiveness, engagement feedback loops) that fix root causes before they show up as regretted attrition.

• Lead with data. Build and use people analytics (funnel conversion, ramp time, performance distribution, attrition/retention by segment) to diagnose problems, prioritize the highest-leverage initiatives, and prove impact.

• Manage and develop the recruiting team. Lead by doing. You'll need a deep enough understanding of the pipeline, process, and data to solve problems alongside your team, while upskilling direct reports and pushing them to own larger pieces of the funnel over time.

Competencies:

Do you have what it takes to build the people systems that let Shiftsmart scale? Here are the attributes you'll need:

• First-Principles Thinker: You don't need a traditional talent or HR background — you might come from finance, consulting, ops, or general management. What matters is that you can take a fuzzy problem (why do people leave in month three? what actually makes onboarding stick?), reason through it from scratch, and build the answer yourself rather than importing someone else's playbook.

• Builder of Solutions, Not Just Processes: You think in terms of scalable systems that address the root cause, not one-off fixes. Whether or not you've built onboarding programs or performance cycles before, you know how to design something repeatable once you understand the problem.

• Self Starter: You're comfortable taking initiative and consistently delivering results in fast-paced, ambiguous environments. You don't wait to be told what to do, you identify the problem, build the plan, and get to work.

• Technical & Data-Driven: You use data to diagnose people problems (funnel conversion, ramp time, attrition) and prioritize accordingly. You're comfortable in Excel/Sheets and modern HRIS/ATS tooling, and you leverage AI tools to work more efficiently.

• Player-Coach: You lead a team, but you're not above doing the work yourself — running an interview loop, rewriting an onboarding doc, or personally diagnosing why a cohort is churning — when that's the highest-leverage thing you can do.

• Direct Communicator: You give and receive feedback candidly and kindly, and you're comfortable telling hiring managers and leadership uncomfortable truths about hiring quality, ramp, or attrition.

Compensation philosophy

To provide greater transparency we share base salary ranges, which are based on role and level benchmarked against similar stage, high growth companies. Offers are determined based on multiple factors including skills, work experience, and relevant credentials.

In addition to competitive salaries and meaningful equity we offer the following benefits:

• Comprehensive healthcare coverage: We cover 100% of employee premiums for medical, dental, and vision care (60-75% for dependents)

• 401(k) match program: We match 100% on the first 3% of your contributions and 50% on the next 2% for a maximum match of 4%

• Generous, fully paid parental and family leave policies

• Pre-tax commuter benefits

• Collaborative office with fully stocked kitchen @ 1 World Trade in Manhattan

Equal opportunity employer

Shiftsmart is committed to creating a diverse environment and is proud to be an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

Operating Principles @ Shiftsmart

Inspired by Leadership Principles @ Amazon

Execution Is Binary

We #GetShiftDone. We take immense pride in both the quality of our work and our relentless determination to deliver on our commitments. If we say we are going to do something, we do it.

We own the outcome with an unstoppable mindset through the finish line and are impatient to move the ball forward. This means we work really hard, execute with urgency, and ruthlessly challenge timelines for anything important. As a result, we do not defer responsibility to other teams or individuals. Instead, we take the problem as far as we can and only when needed ask others for help.

Each time a crisis or opportunity emerges we take the hill as one team, because we are allergic to the words “it can’t be done”.

Missionaries, Not Mercenaries

We before me. We believe in our mission to build a better world for workers. We understand why our work matters and take seriously how it impacts our customers and our partners. This belief permeates everything we do from the strategic to the mundane.

We are energetic, ambitious, and want to win. We constantly raise the standards for ourselves and everyone around us. We show up for our customers, our partners, and most importantly our teammates, and make every effort to build lasting relationships with each of them.

We do not measure success based on our titles or the size of our empires. This also means we put the needs of the business before the details of our job descriptions. Rather than fight for a bigger piece of the pie, we fight to grow the entire thing and recognize this is how to grow our careers too.

Inputs > Outcomes

We work really hard. Fundamentally changing how labor works is not easy. It often requires long days, late nights, and weekends to deliver on our commitments. We lean into this challenge.

We focus on the process. We think in terms of value chains and appreciate that a bad process with a good outcome is simply dumb luck. 

We lead with data. We use facts, not fiction, to build narratives and make decisions. To do this we prepare written memos in advance and resist the urge to engage in endless water cooler what ifs, because we value the time and attention of our teammates.

We hire and develop the best. When we decide to hire a new team member, we do so because we believe they will increase the talent density on our team. We view ourselves as leverage maximizers rather than inconvenience reducers and strive to increase the output of everyone we interact with.

Honesty Over Harmony

We share the truth even when it is painful. We do not, however, share the truth callously to hurt people’s feelings or make them look bad. We also assume positive intent. If someone is not delivering in a way that we need, we ask them and tell them before assuming the worst.

We embrace mutual feedback. As people leaders we care more about our team’s growth and success than how much others like us. As individuals we seek, accept, and apply feedback. We do not give or take feedback personally because we understand it enables us to learn and grow.

We tell the truth to ourselves. We reject a pollyannaish view of our world. Instead if something isn’t going well that we are responsible for, we call it out. And when someone calls out their own truth that may be less optimal, we don’t punish them for it.

We have the meeting in the meeting. If something is broken or we disagree, we call it out and say something in the moment even if it feels uncomfortable to do so. This means that if something is broken, we do not just accept it and complain later.

Invent & Iterate

We are inventors @ heart. We categorically reject the phrase “that is how it’s always been done”, and constantly discover new and better ways to do more with less. This means we are resourceful and often do things that don’t scale, only to create ways to scale them later. We’re builders.

We think BIG. At every level of the company, we embrace big, hairy, audacious, and transformative goals. We fear lack of progress and incremental thinking more than failing to deliver or falling short of an audacious goal. We believe courage means to try without fear and learn without ego.

We do not let perfect get in the way of better. When faced with the choice we prioritize delivering something, even if imperfect, over endless debate and alignment. We embrace good mistakes.