Director of Total Rewards and Analytics at Decagon

About Decagon Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences. Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel. We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others. We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team. DIRECTOR, TOTAL REWARDS About the Role Decagon is looking to hire our first Director of Total Rewards to build and own the foundation of how we attract, reward, and retain world-class talent as we scale. This is a high-impact, zero-to-one role: you'll design the compensation and benefits architecture from the ground up, bring structure and rigor to our equity programs, and serve as the strategic authority on all things total rewards across the company. You'll partner directly with our founders, People leadership, and Finance to ensure our programs are competitive, equitable, and built to scale with us. You May Be a Good Fit If You: - Have 8+ years of experience in compensation, benefits, or total rewards at a high-growth tech or SaaS company - leadership experience is a plus - Have built or significantly rebuilt compensation structures, job architecture, and leveling frameworks — ideally in a fast-moving, pre-IPO environment - Have deep expertise in equity compensation (option plans, RSUs, refresh cycles) and experience supporting equity education and communications for employees - Understand how to design and administer competitive benefits programs, including medical, dental, vision, 401(k), and ancillary programs, while managing vendor relationships and renewals - Are data-driven — you use market data (Pave, Levels.fyi [Upgrade to PRO to see link] etc.) to anchor decisions and can build clean, defensible comp models - Have experience partnering with Finance on headcount planning, comp accruals, and total compensation cost modeling - Are a strong communicator who can distill complex comp concepts for employees, managers, and executives alike - Thrive in ambiguity and can move quickly without sacrificing rigor Even Better If You: - Have worked at a company that scaled from ~100 to 500+ employees and navigated the total rewards complexity that comes with that growth - Have experience with executive compensation and board-level reporting - Have supported international expansion and understand how to structure compensation across multiple geographies - Are familiar with HR tech and compensation tooling (Carta, Pave, Radford, Workday, Rippling, etc.) What You'll Own: - Design and own Decagon's total compensation philosophy, including salary bands, equity guidelines, bonus structures, and benefits programs - Build and maintain a job architecture and leveling framework that creates consistency and clarity across the company - Lead annual and mid-year compensation review cycles, partnering closely with Finance and People Business Partners - Own all equity program administration — from grant processes and refresh cycles to employee education and vesting communications - Manage our benefits programs end-to-end, including open enrollment, broker relationships, and ongoing plan design - Serve as the internal expert on comp and benefits compliance (FLSA, ACA, state-level requirements, etc.) - Partner with Recruiting to build compelling, competitive offers and ensure we're winning top talent at every level - Develop clear communications that help employees understand and value their total compensation package