Otterbrook
About the Company
Our client is a rapidly scaling enterprise AI platform transforming how organizations connect with and serve their customers. Their technology blends natural communication, automation, and intelligence to help leading companies improve efficiency, consistency, and customer experience across high-volume interaction channels.
The platform is already used by thousands of businesses globally to modernize customer engagement, automate workflows, and drive measurable ROI. Backed by top-tier investors, the company has achieved exceptional growth with a lean team and is entering its next major expansion phase.
If you’re motivated by the chance to help scale a cutting-edge AI platform and work directly with a founding team known for rapid execution and technical excellence, this is an opportunity to join at a pivotal stage of growth.
The Role As the
Founding Enterprise Account Executive , you’ll own the enterprise sales strategy and execution as the company scales from early-stage traction to major market adoption. Reporting directly to the CEO, you’ll lead strategic enterprise deals end-to-end, while building the systems, processes, and future team that will power long-term growth.
This is a rare, ground-floor opportunity to define the GTM playbook of one of the fastest-growing companies in enterprise AI. For the right candidate, there’s a clear growth path toward VP of Sales or CRO.
Key Responsibilities
Enterprise Sales Leadership:
Build and own the enterprise sales motion from the ground up, leveraging strong inbound traction and product-led adoption to secure high-value enterprise contracts.
Deal Execution:
Manage complex sales cycles from initial engagement to close, collaborating closely with technical and executive stakeholders.
Strategic Account Development:
Drive ABM strategies, build executive relationships, and create scalable frameworks for expansion and retention.
Revenue Operations:
Implement CRM and data-driven tools to streamline forecasting, reporting, and pipeline management.
Executive Collaboration:
Work directly with the CEO and leadership team to refine GTM strategy and drive revenue growth across enterprise and strategic accounts.
Ideal Background
7+ years of enterprise SaaS sales experience, ideally in high-growth or AI/automation companies.
Proven success scaling revenue from early-stage to $100M+ ARR environments.
Track record of closing complex, multi-stakeholder enterprise deals.
Consultative, solution-oriented sales approach (MEDDICC or similar framework preferred).
Experience in PLG-to-sales-led environments (examples: Vercel, Carta, Ashby, Vanta, Datadog, Asana, Airtable).
Strong business acumen and ability to collaborate across product, engineering, and GTM functions.
High ownership mindset — thrives in fast-paced, founder-led environments.
Competitive Base + Commission + Equity.
100% employer-covered medical, dental, and vision insurance.
$70/day meal credit for onsite workdays.
$200/month wellness or fitness reimbursement.
$300/month commuter stipend.
Compensation Philosophy
Transparent Offers:
Choose from multiple cash–equity balance options — no negotiation required.
Top Talent Focus:
Above-market pay for exceptional performers.
Ownership Culture:
Small team, big impact, meaningful equity.
Performance-Based Growth:
Compensation tied directly to results and contribution.
Interview Process
Intro Call (20 min):
Conversation with a founder to discuss background and experience.
Skills Round (45 min):
Live product-selling exercise.
In-Person Session (3 hrs):
Deep dive with founders and GTM team.
Offer:
Extended to selected finalist.
Seniority Level Director
Employment Type Full-time
Job Function Sales and Business Development
Industries Software Development
#J-18808-Ljbffr
The platform is already used by thousands of businesses globally to modernize customer engagement, automate workflows, and drive measurable ROI. Backed by top-tier investors, the company has achieved exceptional growth with a lean team and is entering its next major expansion phase.
If you’re motivated by the chance to help scale a cutting-edge AI platform and work directly with a founding team known for rapid execution and technical excellence, this is an opportunity to join at a pivotal stage of growth.
The Role As the
Founding Enterprise Account Executive , you’ll own the enterprise sales strategy and execution as the company scales from early-stage traction to major market adoption. Reporting directly to the CEO, you’ll lead strategic enterprise deals end-to-end, while building the systems, processes, and future team that will power long-term growth.
This is a rare, ground-floor opportunity to define the GTM playbook of one of the fastest-growing companies in enterprise AI. For the right candidate, there’s a clear growth path toward VP of Sales or CRO.
Key Responsibilities
Enterprise Sales Leadership:
Build and own the enterprise sales motion from the ground up, leveraging strong inbound traction and product-led adoption to secure high-value enterprise contracts.
Deal Execution:
Manage complex sales cycles from initial engagement to close, collaborating closely with technical and executive stakeholders.
Strategic Account Development:
Drive ABM strategies, build executive relationships, and create scalable frameworks for expansion and retention.
Revenue Operations:
Implement CRM and data-driven tools to streamline forecasting, reporting, and pipeline management.
Executive Collaboration:
Work directly with the CEO and leadership team to refine GTM strategy and drive revenue growth across enterprise and strategic accounts.
Ideal Background
7+ years of enterprise SaaS sales experience, ideally in high-growth or AI/automation companies.
Proven success scaling revenue from early-stage to $100M+ ARR environments.
Track record of closing complex, multi-stakeholder enterprise deals.
Consultative, solution-oriented sales approach (MEDDICC or similar framework preferred).
Experience in PLG-to-sales-led environments (examples: Vercel, Carta, Ashby, Vanta, Datadog, Asana, Airtable).
Strong business acumen and ability to collaborate across product, engineering, and GTM functions.
High ownership mindset — thrives in fast-paced, founder-led environments.
Competitive Base + Commission + Equity.
100% employer-covered medical, dental, and vision insurance.
$70/day meal credit for onsite workdays.
$200/month wellness or fitness reimbursement.
$300/month commuter stipend.
Compensation Philosophy
Transparent Offers:
Choose from multiple cash–equity balance options — no negotiation required.
Top Talent Focus:
Above-market pay for exceptional performers.
Ownership Culture:
Small team, big impact, meaningful equity.
Performance-Based Growth:
Compensation tied directly to results and contribution.
Interview Process
Intro Call (20 min):
Conversation with a founder to discuss background and experience.
Skills Round (45 min):
Live product-selling exercise.
In-Person Session (3 hrs):
Deep dive with founders and GTM team.
Offer:
Extended to selected finalist.
Seniority Level Director
Employment Type Full-time
Job Function Sales and Business Development
Industries Software Development
#J-18808-Ljbffr