Founding Enterprise Account Executive

Wintermeyer Ventures; Chicago (IL); Remote; USD 125,000 - 170,000; Full time

Job summary

Wintermeyer Ventures is building its enterprise sales motion for an AI and B2B SaaS platform. You will own the full sales lifecycle from outbound prospecting to close, collaborating with leadership to bring technical AI solutions to large insurers.

You will build the pipeline, develop the playbook, and drive expansion across enterprise accounts. The ideal candidate has 3–8 years closing B2B SaaS deals, experience with $200k+ ACV, and a startup-first mindset.

Qualifications

• 3–8 years closing B2B SaaS deals at startups.
• At least 1 year closing enterprise deals with $200k+ ACV.
• Experience building outbound pipeline (SDR/BDR).
• Experience selling AI/data/technical products to technical buyers.
• Startup experience and interest in building new sales processes.
• Bachelor's degree or equivalent.
• Track record of tenure with minimal job-hopping.

Responsibilities

• Build and manage an enterprise pipeline from outbound prospecting to close.
• Develop the sales playbook and processes as an early sales team member.
• Partner with leadership on enterprise opportunities and own the sales lifecycle.
• Grow customer accounts through expansion opportunities.
• Navigate multi-stakeholder sales with technical buyers and business leaders.

Skills

Enterprise SaaS sales

Outbound prospecting

Enterprise deals closing

Selling to technical buyers

Startup experience

Account expansion

Education

Bachelor's degree or equivalent

Job description

About the Role

Join an early-stage AI and B2B SaaS team to build its enterprise sales motion from the ground up. You will own the full sales lifecycle, working with company leadership to bring technical AI solutions to large insurance organizations.

What You'll Do

• Build and manage an enterprise pipeline, from outbound prospecting and discovery through demos, negotiation, and close.
• Develop the sales playbook and processes as an early member of the sales team.
• Partner with company leadership on enterprise opportunities and take ownership of the sales lifecycle.
• Grow customer accounts through expansion opportunities.
• Navigate complex, multi-stakeholder sales with technical buyers and business leaders.

What We're Looking For

• Three to eight years of experience closing B2B SaaS deals at startups, including at least one year closing enterprise deals with $200,000 or more in annual contract value.
• Experience building outbound pipeline, including prior SDR or BDR work.
• Experience selling AI, data, or other highly technical products to technical buyers is valuable.
• Startup experience, a demonstrated interest in building new sales processes, and a bachelor's degree or equivalent.
• A track record of reasonable tenure, with at least one year in all but at most one recent role.

Compensation & Benefits

Base salary: $125,000 to $170,000 annually. Visa sponsorship is available.

Location

Remote within the United States. Primary location: Chicago, Illinois.