Sales Development Representative ( + Equity) at Series A AI-native insurance

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

Sales Development Representative

Salary

$70k-$100k + Equity

Company Description

$50M Series A AI-native insurance startup backed by Founders Fund and Bessemer

Job Description

Join a high-intensity team disrupting the $280B insurance market as an early sales hire. Working directly with the CEO, you will drive pipeline for $500k+ ACV contracts in an environment growing 50% month-over-month. This is a rare opportunity to join a Tier 1-backed powerhouse where top performers are fast-tracked for leadership roles.

Location

San Francisco, USA

Why this role is remarkable

• Insane sales velocity with $500k+ ACV contracts and sub-100-day sales cycles; our first two sellers closed $3.8M in just three months.
• Elite pedigree with $50M Series A led by Bessemer and Seed funding from Peter Thiel’s Founders Fund, including the partner early in OpenAI and Scale AI.
• High-reward culture offering top-quartile OTE, uncapped commissions, and zero-barrier support including full relocation and all meals covered.

What You Will Do

• Build and aggressively expand target account lists to drive outbound pipeline through cold calls, email automation, and LinkedIn.
• Own the initial qualification process by running first discovery calls with enterprise insurance carriers to identify high-value revenue opportunities.
• Partner directly with the CEO and SVP of Sales to build the company’s outbound engine and develop new enterprise GTM playbooks.

The ideal candidate

• At least 1-2+ years of experience in an SDR, BDR, or GTM role with a proven track record of generating outbound pipeline.
• Relentless drive and comfort with high-volume outbound activity, including the ability to handle 100+ cold calls per day and live conversations.
• High-agency operator with a competitive background who thrives in an in-person, high-intensity San Francisco environment.

Who are Jack & Jill?

Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

Next steps

Step 1. Visit the job listing.

Step 2. Click 'Talk to Jack', or go straight there: https://www.jackandjill.ai/jobs/sales-development-representative-70k-100k-equity-at-50m-series-a-ai-native-insur-21d9ef91-7d54-4596-b163-6c24573d3512?utm_source=linkedin&utm_medium=job_post&utm_campaign=featured_role_21d9ef91-7d54-4596-b163-6c24573d3512

Step 3. Talk to Jack so he can understand your experience and ambitions.

Step 4. Jack will make sure Jill (the AI agent working for the company) considers you for this role.

Step 5. If Jill thinks you're a great fit and her client wants to meet you, they will make the introduction.

Step 6. If not, Jack will find you excellent alternatives. All for free.

We never post fake jobs

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.