Senior Enterprise Sales Leader (Commercial Insurance)

SmartFinancial · Newport Beach, CA

Base: Not disclosed
OTE: Not disclosed
Posted: 10mo ago

Still open · checked 2h agoon SmartFinancial's careers page

Apply on SmartFinancial →

The job

What you'd do: Win new deals with big insurance companies and insurance brokers, sell more to current ones, and run each deal from first call to signed contract.
Who you'd sell to: Still reading the posting. Check back within the hour.
Where deals come from: Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay: No pay listed at all.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle.
Time on market: Open 317 days. Ask why it's been hard to fill.
Company hiring: 9 sales roles open, hiring at a steady pace.

Red lights

None spotted.

Yellow lights

Open 90+ days. This role has been posted for three months or more. Ask why it's been hard to fill, and whether anyone left it.

Green lights

None spotted.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
This role has been open a while. What's made it hard to fill?
The answer tells you what candidates saw that made them walk.
2.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
3.
What are the base and the OTE for this role?
No point investing hours before you know the number.
4.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
5.
What share of last year's closed deals did reps source themselves?
Shows how much pipeline you'll have to build on your own.
6.
Why is this role open? Did someone leave, or is it new?
New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

1.
Can I see the full comp plan in writing, including clawbacks and accelerators?
What's in writing is what gets paid. Read it before you sign.
2.
Can I see the actual comp distribution for the team last year, not just the OTE?
The spread shows what most reps really take home. OTE is just the target.
3.
I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?
Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

Got an offer from SmartFinancial? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh

Full posting

SmartFinancial is a leading insurance technology platform transforming how consumers and businesses connect with insurance providers. As we expand our commercial insurance footprint, we’re recruiting a senior enterprise seller to own carrier and brokerage partnerships, drive revenue growth, and scale adoption of our commercial insurance marketplace solutions. This is a high-impact, quota-carrying role for someone who understands commercial insurance distribution, carrier and broker economics, and the economics of digital acquisition. Requirements Build and execute a GTM strategy for commercial carriers and brokerages. - Develop and manage a strong pipeline of high-value enterprise prospects. - Lead the full sales cycle: prospecting, discovery, pricing, negotiation, and close. - Prioritize segments with the highest revenue and strategic impact. - Demonstrate deep knowledge of the SmartFinancial Platform and its commercial capabilities. - Cross-sell clicks, leads, calls, audience solutions, and platform integrations. - Expand revenue within existing partners while driving adoption of new products. What We’re Looking For - 5+ years in enterprise sales within commercial insurance, insurtech, carrier distribution, or brokerage partnerships. - Strong understanding of commercial P&C insurance lines (BOP, workers comp, liability, commercial auto, etc.). - Experience selling technology, distribution, or acquisition solutions into commercial carriers or large brokerages. - Proven track record exceeding quota in a consultative, multi-step enterprise sales environment. - Ability to navigate complex carrier organizations and influence senior decision-makers. - Excellent presentation, negotiation, and communication skills. - Analytical mindset with the ability to understand partner KPIs, economics, and growth levers. - Strong sense of ownership and comfort operating in a high-growth, fast-paced environment. Benefits Why Join SmartFinancial - Lead the commercial insurance GTM for one of the fastest-growing insurance marketplaces in the U.S. - Build relationships with senior executives across commercial carriers and brokerages. - Influence product direction and go-to-market strategy across the commercial insurance category. - Competitive $200k+ OTE, with significant variable upside and equity opportunities. - High-growth culture with meaningful career advancement potential. What We Offer - Competitive Base Salary + Commissions + Performance Bonuses - 401(k) with Company Match - Health, Dental, and Vision Insurance - Stock Options - Internal Promotion Opportunities. We believe in growing talent from within What It’s Like to Work Here - World-Class Training and Onboarding - Use the latest technology, tools, and automation systems - Fast-paced, energetic environment where innovation is encouraged - Play ping pong, collaborate with sharp teammates, and enjoy a culture that celebrates hard work and having fun Be part of a rapidly growing tech company reshaping the insurance landscape!

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