CustomGPT.ai
Commercial Account Executive (Full‑Cycle Outbound)
CustomGPT.ai, Needham Heights, Massachusetts, us, 02494
1 day ago Be among the first 25 applicants
Bootstrapped = real equity — no VC math. Your equity actually matters.
Real product‑market fit:
profitable, strong traction, and customers who love our product.
Autonomy + upside:
no bureaucracy, no scripts — just ownership and results.
High‑leverage opportunity:
shape the next chapter of a profitable AI company from the ground up.
Why This Role Exists We’ve built strong product‑market fit and serve hundreds of high‑performing AI customers. We’re now hiring an
Outbound Account Executive
to own the complete sales motion — from outbound to close — targeting SME and Mid‑Market accounts that mirror our most successful customers.
Your mission:
identify, engage, and close these look‑alike accounts , turning outbound strategy into a repeatable, scalable revenue engine. This isn’t a “wait for inbound” role — it’s a builder’s seat focused on outbound creativity, experimentation, and closing new business.
What Makes You a Great Fit
3–10 years of total sales experience , with
1–4 years in a full‑cycle closing role in a Startup Environment.
Proven success in
SME/Mid‑Market SaaS sales , ideally with outbound or self‑sourced pipeline experience.
Builder’s mindset:
you’re scrappy, experimental, and driven to create something new rather than follow a playbook.
Confident working with
AI Champions , Support, Success, and IT leaders — you can build champions and navigate buying committees.
Strong communicator who thrives on ownership, creativity, and measurable impact.
Bonus: experience selling AI, automation, or data‑driven SaaS solutions.
What You’ll Do
Own the full sales cycle:
from targeted outbound prospecting and qualification to demo, business case, negotiation, and close.
Build pipeline from lookalikes:
identify and engage companies similar to our top customers using research, AI tools, and pattern recognition.
Create urgency & ROI:
design success plans and POCs that demonstrate clear business value (e.g., ticket deflection, CSAT, AHT).
Collaborate cross‑functionally:
partner with Product, Success, and Leadership to refine messaging and share learnings from outbound experiments.
Iterate fast:
test sequences, channels, and talk tracks — document what works and shape the outbound motion for scale.
Forecast with discipline:
maintain crisp notes, next steps, and predictable pipeline hygiene (MEDDPICC‑lite).
Impact You’ll Have in 90 Days
Close net‑new deals
sourced entirely from outbound and look‑alike account motions.
Build repeatable outbound patterns
by identifying high‑performing look‑alike customer segments.
Refine messaging and POC frameworks
that demonstrate ROI and accelerate deal velocity.
Establish the foundation
for a scalable outbound sales motion and future team growth.
OTE:
$180K ($90K base + $90K commission), uncapped with accelerators
Equity:
meaningful ownership in a profitable, growing company
Benefits:
health insurance, PTO, and a culture that celebrates learning and winning together
About CustomGPT.ai 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 and hundreds of enterprise teams adopting AI agents across support, success, marketing and sales operations.
Sound like your kind of challenge? We’d love to hear from you — especially if you thrive on ownership, creativity, and building from scratch.
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Sales and Business Development
Industries Technology, Information and Internet
Referrals increase your chances of interviewing at CustomGPT.ai by 2x.
#J-18808-Ljbffr
Bootstrapped = real equity — no VC math. Your equity actually matters.
Real product‑market fit:
profitable, strong traction, and customers who love our product.
Autonomy + upside:
no bureaucracy, no scripts — just ownership and results.
High‑leverage opportunity:
shape the next chapter of a profitable AI company from the ground up.
Why This Role Exists We’ve built strong product‑market fit and serve hundreds of high‑performing AI customers. We’re now hiring an
Outbound Account Executive
to own the complete sales motion — from outbound to close — targeting SME and Mid‑Market accounts that mirror our most successful customers.
Your mission:
identify, engage, and close these look‑alike accounts , turning outbound strategy into a repeatable, scalable revenue engine. This isn’t a “wait for inbound” role — it’s a builder’s seat focused on outbound creativity, experimentation, and closing new business.
What Makes You a Great Fit
3–10 years of total sales experience , with
1–4 years in a full‑cycle closing role in a Startup Environment.
Proven success in
SME/Mid‑Market SaaS sales , ideally with outbound or self‑sourced pipeline experience.
Builder’s mindset:
you’re scrappy, experimental, and driven to create something new rather than follow a playbook.
Confident working with
AI Champions , Support, Success, and IT leaders — you can build champions and navigate buying committees.
Strong communicator who thrives on ownership, creativity, and measurable impact.
Bonus: experience selling AI, automation, or data‑driven SaaS solutions.
What You’ll Do
Own the full sales cycle:
from targeted outbound prospecting and qualification to demo, business case, negotiation, and close.
Build pipeline from lookalikes:
identify and engage companies similar to our top customers using research, AI tools, and pattern recognition.
Create urgency & ROI:
design success plans and POCs that demonstrate clear business value (e.g., ticket deflection, CSAT, AHT).
Collaborate cross‑functionally:
partner with Product, Success, and Leadership to refine messaging and share learnings from outbound experiments.
Iterate fast:
test sequences, channels, and talk tracks — document what works and shape the outbound motion for scale.
Forecast with discipline:
maintain crisp notes, next steps, and predictable pipeline hygiene (MEDDPICC‑lite).
Impact You’ll Have in 90 Days
Close net‑new deals
sourced entirely from outbound and look‑alike account motions.
Build repeatable outbound patterns
by identifying high‑performing look‑alike customer segments.
Refine messaging and POC frameworks
that demonstrate ROI and accelerate deal velocity.
Establish the foundation
for a scalable outbound sales motion and future team growth.
OTE:
$180K ($90K base + $90K commission), uncapped with accelerators
Equity:
meaningful ownership in a profitable, growing company
Benefits:
health insurance, PTO, and a culture that celebrates learning and winning together
About CustomGPT.ai 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 and hundreds of enterprise teams adopting AI agents across support, success, marketing and sales operations.
Sound like your kind of challenge? We’d love to hear from you — especially if you thrive on ownership, creativity, and building from scratch.
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Sales and Business Development
Industries Technology, Information and Internet
Referrals increase your chances of interviewing at CustomGPT.ai by 2x.
#J-18808-Ljbffr