Mid-Market/Enterprise AE

About Sybill: B2B AEs spend only 1.5 hours a day on customer calls—the rest is wasted in back-office admin work. Sybill automates away this drudgery, empowering sales reps to focus on what matters most: building relationships and closing deals. We don’t just take meeting notes—Sybill automatically creates and manages to-do lists from both calls and emails and then helps auto-execute those tasks using AI. This includes updating CRM, sending follow-up emails, scheduling follow-up meetings, researching information, customizing collaterals (decks, one-pagers, RFPs), and much more. Sybill helps reps to close more while doing less. And we envision that Sybill will enable an AE to close 200% more revenue. We have raised $15M to make this assistant of the future a reality for AEs. With 750+ happy customers, 70% of our revenue comes from word-of-mouth through our PLG offering. We have a small and mighty team with some of the sharpest and most driven minds working together. We combine proprietary models and foundational LLMs to power our agentic technology, delivering highly accurate results. Who Thrives at Sybill? We're looking for people who: Keep things moving and keep them simple: You value speed over perfection. You cut through complexity, focus on what matters, and keep raising the bar—every single day. Care deeply about outcomes: You’re driven by real results. Not effort, not activity—impact. For our users, for the business, and for the team. Collaborate like we're one team: You share the wins, step up to help, and know that none of us succeed unless all of us do. Say the hard things, and stay open: You believe in honesty, transparency, and learning from every win and every mistake. Challenges don’t scare you—they push you to get creative. The Opportunity As the Head of Sales at Sybill, you will own and drive revenue growth across our mid-market and enterprise segments. You’ll be responsible for designing, executing, and continuously optimizing our sales strategy— not by managing people, but by leading from the front. You’ll personally handle key deals, refine messaging and positioning through real-world feedback, and work cross-functionally to shape how Sybill is sold, scaled, and adopted across organizations. This role is for a high-performing individual contributor who thrives on execution, experimentation, and impact—not people management. You’ll operate as a player-coach, a founder-level operator who builds repeatable systems by doing, learning, and iterating. You’ll help define how Sybill’s cutting-edge AI transforms how AEs sell. What you’ll do: Own the full sales funnel—from prospecting and qualification to negotiation and close—across mid-market and enterprise accounts. Design and iterate on Sybill’s go-to-market, optimizing messaging, discovery, and deal cycles. Consistently exceed targets while maintaining a rigorous, metrics-driven approach to forecasting and pipeline management. Partner closely with the founders, marketing, product, and customer success to align GTM strategy, accelerate deal velocity, and identify new market opportunities. Leverage AI tools (including Sybill itself) daily to scale your productivity, prospect smarter, and close faster. Represent the voice of the customer internally, shaping product direction and positioning with real-time insights. What we’re looking for: 4+ years of experience in a closing role, with at least 2 years in SaaS sales. Tenacious about winning deals - multithreading, flipping challenges into opportunities, and breaking through obstacles excites you. Comfortable navigating uncertainty and ambiguity, proactively making strategic decisions, and ready to dive in at any level to drive results. Passionate about the potential of AI in sales and an active user of tools like ChatGPT. You're resourceful, proactive, and adept at leveraging AI to streamline your day-to-day work. Operate with high horsepower, have strong problem-solving skills, are adept at frequent context switching, effectively manage working on multiple projects at once with expansive ownership, and ruthlessly prioritize. Possess exceptional presentation and communication skills. A proven growth mindset; you learn rapidly, iterate constantly, and proactively adapt to market and competitive shifts. Honest, transparent, and collaborative. You embrace giving and receiving direct feedback to continuously improve. Why Join Us We believe Sybill should be your biggest career accelerant yet. We'll deliver on this by tackling hard problems together, giving you real ownership, and pushing you to grow beyond your comfort zone. If you're ready to match this ambition with your drive, let’s talk. Here’s what you can expect: Make an Impact : Your work will directly shape our brand presence and business growth. Room to Innovate : We welcome big ideas and give you the freedom to experiment. Fast-Paced Environment : We move quickly and learn just as fast. Early-Stage Culture : Grow with us, and help build something that can scale globally. What We Offer: Competitive compensation + comprehensive Health/Dental/Vision insurance + equity Growth & Autonomy: Small team, big impact—grow alongside us! Flexible PTO: We’re big fans of working hard and recharging when needed! Company Offsite: Our annual offsite for collaboration and team fun! Location & Work: Remote-friendly, with a preference for hybrid/in-person setups. Flexible hours—whatever it takes to close your deals.