Founding Account Executive

The Role

As our founding Account Executive, you will build and own the agency sales motion at Hedge.

You will sell Hedge’s wholesale brokerage partnership to independent retail insurance agencies and commercial producers. You will own the relationship from the first conversation through qualification, close, onboarding, and the agency’s first qualified submissions.

This is not a hand-off role. You will receive meetings from our SDR team, but you will also build your own pipeline through direct outreach, referrals, conferences, and industry relationships.

A signed agreement is not the finish line. Success means earning the trust of agency owners and producers, understanding where their accounts are getting stuck, and turning the relationship into recurring submission flow.

This role is focused on retail-agency distribution. Carrier appointments and placement execution are owned by our markets and brokerage teams.

What You’ll Do

• Own the full agency sales cycle: prospecting, qualification, discovery, presentation, negotiation, close, onboarding, and activation

• Build self-sourced pipeline through calls, email, LinkedIn, referrals, conferences, and industry relationships

• Run structured discovery with agency owners, commercial producers, practice leaders, and operations executives

• Understand each agency’s book, target industries, difficult placements, existing market access, and decision-making process

• Explain how Hedge helps retail agents obtain faster, stronger specialty and E&S coverage for their clients

• Convert qualified meetings into active agency relationships and initial submission opportunities

• Work with the brokerage team to ensure clean handoffs and a strong first placement experience

• Manage 30 to 50 active opportunities with disciplined CRM hygiene and follow-up

• Build account plans and navigate multiple stakeholders within larger agencies

• Handle objections involving existing wholesale relationships, appetite, responsiveness, coverage, and trust

• Develop sales materials, discovery frameworks, scripts, sequences, and onboarding processes

• Use AI, software, and automation to research accounts, prepare for calls, follow up, and manage pipeline

• Feed agency feedback into Hedge’s product, placement, appetite, and market-access strategies

• Represent Hedge at insurance conferences, agency meetings, and industry events

• Help recruit and train future SDRs and Account Executives

What Success Looks Like

During your first 30 days:

• Learn Hedge’s target agency profile, value proposition, appetite, and brokerage workflow

• Build your target-account list and begin running discovery calls

• Establish clean CRM, follow-up, and pipeline-management habits

During your first 60 days:

• Build a healthy combination of self-sourced and SDR-generated opportunities

• Run the complete discovery, presentation, objection-handling, and closing process

• Convert initial agencies into active onboarding and submission opportunities

During your first 90 days:

• Close and activate your first agency relationships

• Generate qualified submission flow from those relationships

• Demonstrate a repeatable sales process that can be documented and scaled

• Maintain accurate pipeline visibility and reliable forecasting

What You Bring

• 3+ years of full-cycle B2B sales, insurance distribution, agency sales, wholesale brokerage development, insurtech, fintech, or vertical SaaS experience

• A demonstrated record of meeting or exceeding a closing quota

• The ability to explain your quota, attainment, deal size, sales cycle, and self-sourced pipeline using specific numbers

• Strong discovery, presentation, negotiation, and objection-handling skills

• Comfort selling to small and mid-sized businesses with multiple stakeholders

• The ability and willingness to generate your own pipeline

• Strong written communication and professional follow-through

• Disciplined CRM, pipeline-management, and forecasting habits

• Comfort selling a relationship and service rather than relying exclusively on product features

• Interest in building a sales process from scratch

• Experience selling to insurance agencies or brokers is strongly preferred

• An active P&C producer license is a plus; Hedge will support licensing if needed

• Willingness to travel and work in person with a small, high-urgency team

What We Offer

• $110,000 to $150,000 base salary

• $180,000 to $250,000 on-target earnings with uncapped commission

• Meaningful equity

• Health benefits

• Direct access to the founders and influence over distribution strategy

• A path to sales leadership as the team grows

• In office in San Francisco, six days a week

• The opportunity to build the agency distribution engine behind a defining insurance company

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Interview Process

Our process is fast and practical.

1. Founder conversation

A 30-minute conversation about your sales background, performance, working style, and why you want to build agency distribution at Hedge.

2. Sales record deep dive

We will review your quota, attainment, average deal size, sales cycle, self-sourced pipeline, and several deals you personally won or lost. We are looking for specific evidence of performance rather than general sales language.

3. Live agency working session

We will give you a hypothetical independent commercial insurance agency. During the session, you will research the account, identify the relevant stakeholders, plan the discovery call, and explain how you would position Hedge.

This is completed live. There is no take-home assignment.

4. Discovery and objection-handling simulation

You will run a simulated agency sales call with one of the founders. We will evaluate your preparation, questioning, listening, positioning, judgment, follow-through, and response to objections.

5. Final founder conversation

We will discuss compensation, commission, equity, working style, and what success should look like during your first 30, 60, and 90 days.

Our goal is to get from the first conversation to an offer in approximately five days when there is strong mutual fit.