CustomGPT.ai
Commercial Account Executive (Full‑Cycle Inbound)
CustomGPT.ai, Needham Heights, Massachusetts, us, 02494
CustomGPT.ai is a profitable,
bootstrapped
AI SaaS company that lets enterprises deploy custom AI agents on their own data—fast, secure, and with real ROI. We already serve
1,500+ active paying subscriptions
on self‑serve and have strong enterprise traction.
Why this role exists We have
significant inbound interest
and large pools of past demand (free trials, churned, stalled POCs, and quiet departmental usage). We’re hiring a
full‑cycle Commercial AE
to convert that demand into revenue across
SMB & Mid‑Market
(typical deals
$25K–$100K ).
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, churned, 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; land and expand by department.
Partner internally: collaborate with Product/Success and work closely with
Head of Sales
on pipeline strategy and execution.
Forecast with precision: maintain crisp notes, 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.
You’ve sold
SMB/Mid‑Market
SaaS in the
$25K–$50K
range and can point to repeatable wins.
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/procurement.
Impact you’ll have in 90 days
Revive and close a subset of high‑intent pools (past trials, closed‑lost, churned, 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.
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.
Meaningful equity in a profitable, growing company.
Health, PTO, and a team that cares about winning together.
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Sales and Business Development
Industries Technology, Information and Internet
#J-18808-Ljbffr
bootstrapped
AI SaaS company that lets enterprises deploy custom AI agents on their own data—fast, secure, and with real ROI. We already serve
1,500+ active paying subscriptions
on self‑serve and have strong enterprise traction.
Why this role exists We have
significant inbound interest
and large pools of past demand (free trials, churned, stalled POCs, and quiet departmental usage). We’re hiring a
full‑cycle Commercial AE
to convert that demand into revenue across
SMB & Mid‑Market
(typical deals
$25K–$100K ).
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, churned, 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; land and expand by department.
Partner internally: collaborate with Product/Success and work closely with
Head of Sales
on pipeline strategy and execution.
Forecast with precision: maintain crisp notes, 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.
You’ve sold
SMB/Mid‑Market
SaaS in the
$25K–$50K
range and can point to repeatable wins.
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/procurement.
Impact you’ll have in 90 days
Revive and close a subset of high‑intent pools (past trials, closed‑lost, churned, 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.
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.
Meaningful equity in a profitable, growing company.
Health, PTO, and a team that cares about winning together.
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Sales and Business Development
Industries Technology, Information and Internet
#J-18808-Ljbffr