VP, People Services

Location: United States In 2008, Propeller reinvented the way venture-stage companies build finance teams, and in the process we defined the category the market now calls fractional. Today we are building what comes next: a professional services firm where human judgment and AI-enabled intelligence work as one system. The technology is moving fast. The people side is harder. AI changes what our teams produce, how engagements are staffed, what a career path looks like, and what great looks like in every seat. Firms that treat that as a software rollout will stall. Firms that lead their people through it deliberately will define the next decade. We are hiring the leader who will make that change stick at Propeller. You will be the strategic people partner to our CEO and leadership team: someone who has lived inside a professional services business, ideally finance and accounting, who understands that the expertise, judgment, and client relationships of our people are what clients actually buy, and who has a strong point of view on why driving people change is harder than driving technology change and what it actually takes. This role has a second dimension. Our clients are the same founders and operators who need HR infrastructure as they scale, and many already rely on Propeller for payroll. You will build that foundation into a People Services practice with its own P&L: payroll at the core, augmented by the policies, handbooks, compliance, and HR advisory that small and growth-stage companies need but are not ready to hire for. This is a leadership role for someone ready to build both a function and a practice, not just run a department. Who We Are Today, Propeller's 250+ professionals serve as the embedded finance and accounting partner to some of the most iconic emerging companies in Consumer, Technology, Blockchain, and Business Services. All are fulltime employees, across three continents; none are contractors or freelancers. Behind us: 1,500+ companies served, $105B+ in enterprise value created, 26 unicorn alumni, and $29B+ raised. Ahead of us: the transformation of professional services through AI-enabled intelligence. Our embedded teams integrate seamlessly into client operations in multi-year partnerships. We attend weekly leadership meetings, participate in board prep, collaborate on strategic decisions, and have direct access to client CEOs and CFOs. This embedded positioning creates trust, access, and influence that traditional providers never achieve. PropellerOS, our financial operating platform, combines human judgment, precision accounting, data infrastructure, and AI-enabled insight to transform finance from a back-office function into the central nervous system of growth. The system enables finance-grade standards of lineage, reconciliation, auditability, and explainability, with a named human accountable for every number we ship. Key Responsibilities Most HR leadership roles emphasize one dimension. This role requires three. In a professional services firm, the people are the product. Every decision about hiring, development, compensation, and role design shows up directly in client experience, retention, and the reputation that drives referrals. At the same time, AI is reshaping the work itself. The market treats the internal HR leader, the change leader, and the HR services entrepreneur as three separate jobs. At Propeller they are one, and each makes the others stronger. Strategic People Partner You are a member of the leadership team and the strategic partner to our CEO and practice leaders on everything people. You understand what creates value in a professional services business: the depth of client relationships, the continuity of the teams that serve them, the expertise that compounds over a career, and the institutional knowledge that has to outlast any one person. You build the workforce plan that keeps talent ahead of growth, the career architecture that lets Controllers and CFOs grow on parallel tracks rather than one ladder, and the compensation and performance systems that reward client impact and the outcomes clients pay for. You lead and guide our internal People team, including our recruiting, HR, and compliance leads: you set the strategy, standards, and priorities, and they run execution in their areas. You earn credibility with delivery teams by connecting with them at their level: you understand their work, their clients, and their pressure. If you see HR primarily as administration and compliance, this isn't your role. • Serve as strategic advisor to the CEO and leadership team on organization design, workforce planning, and talent strategy. • Lead and develop the internal People team (recruiting, HR, and compliance), guiding strategy and standards while team leads own day-to-day execution. • Design the career architecture, compensation, and performance systems for client-facing professionals across all practices. • Shape talent strategy for attracting, developing, and retaining the expertise our clients rely on, working through our recruiting lead. • Ensure Propeller's own HR, payroll, benefits, and employment compliance are best-in-class, so we run internally what we sell externally. Transformation Leader You own the people side of Propeller's transformation into an AI-enabled firm. You redesign roles as AI takes on the mechanical work, build the AI fluency programs that move every team member from awareness to daily practice, and reshape performance expectations so the new behaviors are the ones that get recognized and rewarded. You know that resistance is rarely about the tool; it is about identity, trust, and what people believe the change means for them. You bring a clear, tested point of view on how to lead through that, and you hold leaders accountable for doing it with you. You also partner with our Transformation practice to bring change management to client system and process implementations, where the people side decides whether the technology delivers. If your change playbook is a launch email and a training deck, this isn't your role. • Lead the people side of Propeller's AI transformation: role redesign, AI fluency training, change management, and adoption measurement. • Redefine what great looks like in each role as the work shifts from producing outputs to exercising judgment. • Partner with practice leaders and the Transformation practice to bring change management capability to client engagements. Practice Builder You own the People Services practice end to end: offering, pipeline, delivery, and P&L. You accelerate our existing payroll services and build around them the HR services small and growth-stage companies need: handbooks and policies, multi-state compliance, onboarding and offboarding, compensation benchmarking, benefits guidance, and fractional HR leadership. You package and price those services, sell them into our existing client base alongside our embedded finance teams and through our referral network, and build a lean delivery team that runs them to Propeller's standards. You think like a business owner. If you have never carried a number, this isn't your role. • Own the financial performance of the People Services practice: revenue, margins, client retention, and profitability. • Grow payroll services and launch complementary HR offerings (policies, handbooks, compliance, advisory) for small and growth-stage clients. • Drive business development in coordination with our GoToMarket team, embedded client teams, and referral partners. • Use AI and automation in service delivery, and codify what works so the practice scales without adding headcount linearly Skills, Knowledge & Expertise 15+ years in HR and People leadership, with at least 7 years as head of HR or senior strategic HR partner in a professional services firm. Finance, accounting, or advisory firm experience strongly preferred. • A strong, articulated point of view on transforming a professional services business, and on why people change is harder than technology change. You can walk us through a transformation you led: what worked, what broke, and what you would do differently. • Direct experience building or running an HR services offering for small companies (fractional HR, HR consulting, payroll or PEO provider, or similar), including pricing, selling, and delivering it. • Track record leading HR functions through other leaders: guiding recruiting, HR, and compliance leads rather than doing the work yourself. • Deep working knowledge of payroll operations: multi-state payroll and tax, benefits administration, and the major small-business payroll and HRIS platforms. • Command of US employment law and multi-state compliance; experience supporting employees across multiple countries is a plus. • Experience designing compensation, career paths, and performance systems for client-facing professionals. • Demonstrated AI fluency: you use AI in your own HR workflow today and can show us how it changes what you produce. • Commercial instinct: comfortable owning a P&L, building pipeline, and closing business. • Executive presence and credibility with both senior leadership and delivery teams; comfortable delivering difficult messages with clarity. • SPHR or SHRM-SCP preferred. Professional Services Expertise You understand how professional services firms work: why client trust and team continuity are the real assets, how reputation and referrals are earned engagement by engagement, the career expectations of credentialed professionals, and the tension between developing people and serving clients. You know what it takes for a CPA or controller to trust a change in how their work gets done. Experience in a finance and accounting firm, Big 4, or advisory practice is strongly preferred; experience serving small and growth-stage companies as clients is a plus Job Benefits • Base salary range $210,000 - $250,000 + significant variable compensation tied to People Services practice performance and new business. • Equity participation. • Investment in your development: AI/automation training, executive coaching, and access to Propeller's network. • Remote-flexible with travel for team leadership, client meetings, and conferences. Current Benefits Offered: Generous Paid Time Off and Holiday pay, Comprehensive health benefits plus dental, vision, short and long-term disability, and life insurance. HSA contribution, Paid Family Leave, 401k match and Remote Work. We also help you grow in your professional life