Mid-Market/Enterprise AE
About Sybill
Most sales tools log activity: calls, CRM notes, activity feeds. Sybill learns what actually drives a deal to won or lost in your organization, and then acts on it: meeting prep, detailed follow-ups, immediate CRM updates, custom collateral, deal strategy, accurate forecasts, and rep coaching. It delivers the last mile that other AI leaves sitting on the rep's to-do list.
That works because of what's underneath. Most GTM AI wires an LLM straight to raw data and hopes for the best. We spent 18 months building the deep context layer in between - so Sybill knows who each buyer is across every call, email, Slack thread, and Google doc; what led to deal wins and losses before this one; and what worked the last time your team was in this spot. It's the difference between reasoning from a transcript and reasoning from experience, and it means the product gets sharper with every deal you run.
That's why 800+ revenue teams run on Sybill - including Warmly, Smartcat, Beehiiv, and Tribe - and why we've replaced Gong at 25+ companies this year. Reps save 10+ hours a week on admin, manage 2-5x more pipeline, and ramp 50% faster. For an AE, that means a product prospects can test on their own data and choose on the merits, a real category argument to make instead of a feature bake-off, and buyers - CROs, VPs of Sales, and RevOps - who are actively rethinking their stack right now.
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
Sell what you truly believe in. Very rarely does an AE get to sell a product they use daily, that literally helps them make money, and where AI simply works, instead of being a wrapper or just smoke and mirrors.
As a Mid-Market/Enterprise Account Executive at Sybill, you’ll be responsible for executing and continuously optimizing your sales approach by taking full ownership of your pipeline and closing deals.
You’ll personally handle full-cycle opportunities, self-source high-quality pipeline, refine messaging through real-world feedback, and work cross-functionally to show how Sybill is adopted across organizations. This role is for a high-performing individual contributor who thrives on execution, proactive outreach, and impact.
You’ll help demonstrate how Sybill’s cutting-edge AI transforms how AEs sell.
What you’ll do:
Lead deals end-to-end from sourcing pipeline and qualifying prospects to negotiation and close - across mid-market and enterprise accounts.
Consistently exceed targets while maintaining a rigorous, metrics-driven approach to forecasting and personal pipeline management.
Design and iterate on your personal outreach and discovery process, optimizing messaging and shortening deal cycles.
Partner closely with marketing, product, and customer success to align on lead follow-up, accelerate deal velocity, and capture new opportunities.
Leverage AI tools (including Sybill itself) daily to scale your productivity, self-source smarter, and close faster.
Represent the voice of the customer internally, sharing real-time market insights with product and GTM teams.
What we’re looking for:
3+ years of experience in a full-cycle closing role, with at least 2 years in SaaS sales.
A proven track record of self-sourcing pipeline and prospecting into targeted mid-market and enterprise accounts. You will have support from marketing in building the pipeline, but you don’t hesitate to self-source to hit your number.
Tenacious about winning deals - multithreading, flipping challenges into opportunities, and breaking through obstacles excites you.
Comfortable navigating uncertainty and ambiguity, proactively driving your own activity, and taking total ownership of your target.
Passionate about the potential of AI in sales and an active user of tools like ChatGPT/Claude Cowork/Clay, etc. 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 multiple deals at once, 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.