Job Description
CustomGPT.ai is a profitable, bootstrapped AI SaaS company that lets SMEs deploy custom AI agents on their own data — fast, secure, and with real ROI. We already serve thousands of paying customers on self-serve and have strong enterprise traction.
Why this role exists
We have significant inbound interest and large pools of past demand: past enterprise-requests, 300+ new free trials per month, 100,000+ scored leads in our database, plus stale SQLs and closed-lost accounts sitting unworked. We're hiring a full-cycle Account Executive to convert that warm (and cold) demand into revenue across SMB & Mid-Market (typical deals $25K–$75K).
What you'll do
- Own the full cycle: qualify, discovery, demo, business case, champion building, negotiation, and close.
- Work the warm pools: inbound hand-raises, past trials, closed-lost, stale SQLs, and expansion within existing self-serve logos.
- Create urgency: build success plans and POCs that move deals from interest → value → signature.
- Multi-thread: engage buyers across Support, Success, IT, and Data; (across Email, Linkedin, Phone)
- Use AI on the back end: Claude Code for account research, scoring, discovery prep, ROI modeling, and follow-up.
- Human on the front end of every call (NOTE: Human ALWAYS sits on top of the AI -- no AI slop!)
- Partner directly with the CEO: Monday pipeline review is run by the CEO personally; CEO is exec sponsor on every $50K+ deal.
- Forecast with precision: maintain crisp deal data in Hubspot, next steps, and dates; run MEDDPICC-lite hygiene.
What makes you a great fit
- 5–10 years experience with 3–5+ years closing in startup environments (sub-200-employee SaaS).
- You've sold SMB/Mid-Market SaaS in the $25K–$100K range and can point to repeatable wins.
- AI-native workflow: you use Claude Code (or equivalent) daily on real accounts, not as an experiment.
- Builder's mindset: you write the playbook, you don't wait for one. You like speed, experiments, and owning a number.
- No big-company motion: we're not looking for heavy territory bureaucracy. You thrive in lean, fast, and hands-on.
- Comfortable selling to AI Champions / Support / Success / IT leaders, building champions, and navigating security and procurement.
- Integrity at the "I'd raise the issue before you had to ask me" bar: clean attainment, transparent comp history, no sandbagging.
Impact you'll have in 90 days
- Revive and close a subset of high-intent pools (past trials, closed-lost, stale SQLs, current self-serve active subscriptions).
- Deploy and scale our existing POC flavors with clear ROI targets (e.g., deflection / CSAT / AHT), and iterate to accelerate time-to-value.
- Identify additional high-intent pools and run high-value motions to drive closes (e.g., product-qualified leads, departmental adopters, dormant trials).
How we're different
- Bootstrapped = meaningful equity: no "VC math." If we win, your equity actually matters.
- Real product-market fit: steady inbound + a customer base hungry for AI agents.
- Direct to CEO: no middle management layer. Weekly pipeline review with the CEO personally.
- High leverage: you'll close revenue from existing interest and shape the motion for scale.
Compensation & benefits
- OTE: $180K (Base: $90K + $90K at-target commission); uncapped with accelerators (1.5× above 100%, 2× above 150%).
- Stretch: $200–220K OTE for exceptional candidates.
- Meaningful equity in a profitable, growing company — no VC dilution, no liquidation preferences.
- Health, PTO, and a team that cares about winning together.