---
title: 'Mid-Market/Enterprise AE at Sybill AI'
canonical: 'https://feeny.ai/job/mid-market-enterprise-ae-sybill-ai-north-vfc9p7z69m8k'
type: 'job'
last_seen: '2026-09-12'
---

# Mid-Market/Enterprise AE at Sybill AI

- **Company:** Sybill AI
- **Location:** North, United States
- **Compensation:** $170k–$240k
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2025-04-21
- **Last confirmed live:** 2026-09-12
- **Apply:** https://jobs.ashbyhq.com/sybill-ai/0b7dda99-80d7-4f6c-a461-0d0fed238035

## Job description

## 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.

## About Sybill AI

## Company Overview
- **One-liner**: Sybill provides an AI sales assistant that automates administrative tasks and delivers deal-specific insights to help revenue teams win more deals.
- **Entity Type**: Private (Series A)
- **Headquarters**: Mountain View, California, USA
- **Founded**: 2020
- **Founders**: Gorish Aggarwal, Nishit Asnani, Soumyarka Mondal, Mehak Aggarwal

## Core Business
- **Industries**: Sales technology, artificial intelligence, revenue intelligence, sales enablement
- **Target Customers**: B2B sales teams across SMB and enterprise segments (over 850 revenue teams use Sybill)
- **Mission**: “Empower B2B reps to sell twice as much” by reducing administrative burden and surfacing winning playbooks

## Products & Services
- **Sybill AI Sales Assistant (SaaS)**: An AI platform that records and analyzes sales conversations (calls, emails, messages), auto-generates follow-ups, updates CRM fields, surfaces deal risks, and provides coaching and account strategy recommendations. It learns what wins at a company and helps every rep execute the same playbook.
- **API & MCP Integration**: Customers can send deal intel to their data stack or ingest custom data sources. Also available via Model Context Protocol (MCP) for AI agents.
- **Deal Workspace**: A centralized view of all deals showing stakeholders, objections, risks, and next steps.

## Market Standing
- **Valuation**: Not disclosed (last raise: $11M Series A in July 2024)
- **Total Funding**: $14.5M (Seed + Series A)
- **Key Metric**: Annual Recurring Revenue grew from $100K to $1M in 9 months (2023); over 500 paying customer teams as of mid-2024
- **Notable Investors**: Greycroft (lead Series A), Neotribe Ventures, Powerhouse Ventures, Uncorrelated Ventures
- **Growth Signals**: 30 employees (doubled from previous year), plans to reach 40 by end of 2024; 60-70% of new revenue comes from referrals or reps taking Sybill to new companies; customers in 30+ countries

## Competitive Advantages
- **Deal-level Context Graph**: Sybill’s custom RAG pipeline analyzes all calls and emails on a deal, not just isolated transcripts, providing nuanced insights and reducing hallucinations.
- **Playbook Memory**: The platform captures winning patterns (objection handling, sequence, stakeholder mapping) so that institutional knowledge doesn’t leave when a top rep departs.
- **End-to-End Automation**: Unlike point tools (pure notetakers or CRM automation), Sybill handles entire workflows from call recording to CRM updates to follow-ups, acting as a true assistant.
- **SOC 2, GDPR, ISO 27001, PCI Compliant**: Strong security posture required by enterprise buyers.

## Strategic Focus
- Continue developing the AI assistant to handle more complex sales workflows
- Hire aggressively (targeting 40 employees) to accelerate product development and go-to-market
- Expand customer base via word-of-mouth and “bring your own tool” referrals
- Deepen integrations with CRM, Slack, email, and calendar ecosystems

## Why Work Here
- **Culture**: Described as “AI geeks and problem-solvers” on a mission to fix sales admin. The team values impact, speed, and innovation.
- **Remote/Hybrid**: Remote-OK roles listed; office location in Mountain View, CA.
- **Perks**: Flat structure, opportunities to work on cutting-edge AI (RAG, context graphs), direct impact on product direction.
- **Current Openings** (as of 2026): Senior ML Engineer, Senior React Developer, SMB Account Executive, Staff Software Engineer (Full-Stack), HR & Admin Specialist, Senior Visual Designer, Marketing roles (see careers page).
- **Diversity**: “Shine as your unique self and feel right at home” – inclusive environment emphasized.

## Sources
1. [sybill.ai (main site)](https://www.sybill.ai/)
2. [sybill.ai (About Us)](https://www.sybill.ai/about-us)
3. [sybill.ai (Careers)](https://www.sybill.ai/careers)
4. [techcrunch.com (Series A announcement)](https://techcrunch.com/2024/07/31/sybill-raises-11m-for-its-ai-assistant-that-helps-salespeople-reduce-administrative-burden/)
5. [tracxn.com (Sybill AI company profile)](https://tracxn.com/d/companies/sybillai/__yyAyZxFTd0hDRvNQvyNffCi43OefZUuBLJISvv1fNpQ)

## Other roles at Sybill AI

- [Head of Demand Generation](https://feeny.ai/job/head-of-demand-generation-sybill-ai-north-8dmwmsj43gjz) — North, United States
- [RevOps Lead](https://feeny.ai/job/revops-lead-sybill-ai-mountain-view-0trfkqn9kf2e) — Mountain View, CA
- [Growth Marketing Lead](https://feeny.ai/job/growth-marketing-lead-sybill-ai-mountain-view-k29qfwbtvj55) — Mountain View, CA
- [Product Designer](https://feeny.ai/job/product-designer-sybill-ai-mountain-view-w8fs8kjk13nt) — Mountain View, CA
- [Your Next Role](https://feeny.ai/job/your-next-role-sybill-ai-mountain-view-59fh1vfh1e4m) — Mountain View, CA
- [Staff AI Research Engineer](https://feeny.ai/job/staff-ai-research-engineer-sybill-ai-mountain-view-q148s6b9d67q) — Mountain View, CA