Outdoorsy

Roamly - Sales Manager, Insurtech

Outdoorsy • $75K — $150K *
Austin, TX 78745In-Person
Finance & Insurance
Less than 5 years of experience
Today
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Job Overview by Ladders

Qualifications

  • 3+ years of sales leadership experience in fast-paced, inside sales environments.
  • Active Property & Casualty (P&C) or General Lines insurance license preferred.
  • Strong proficiency with CRM tools like Close.ai, Salesforce, or HubSpot.
  • Expertise in coaching teams on consultative sales techniques and clear communication.
  • Ability to thrive in a rapidly evolving startup environment.
  • Willingness to work from Austin, TX, or San Francisco, CA, per hybrid guidelines.

Responsibilities

  • Lead, mentor, and develop a team of licensed Insurance Account Executives to achieve sales targets.
  • Conduct coaching sessions, including call reviews and script analysis, to enhance team performance.
  • Monitor key sales metrics and adjust strategies based on data for improved outcomes.
  • Collaborate with Sales Development and Marketing teams to optimize lead quality and conversion processes.
  • Ensure team compliance with underwriting guidelines and current insurance regulations.
  • Foster a competitive and collaborative team culture focused on shared successes.

Benefits

  • Opportunity for personal growth in an early-stage company.
  • Competitive salary structure with uncapped commission potential.
  • Equity compensation available as part of the package.
  • Comprehensive health and welfare benefits, including 401(k) match.
  • Dynamic office culture with events like Happy Hours and team-building activities.
  • Promotes work-life balance with RV rental discounts and supportive policies.
Full Job Description
On-Target Earnings (OTE): $150,000

About the Role

As our Sales Manager, you will lead the closing team responsible for converting warm inbound inquiries and outbound pipelines into bound insurance policies.

You will directly manage and coach a high-volume team of licensed Insurance Account Executives (AEs). This role requires a unique mix of high-energy leadership, rigorous data tracking, and a proven track record in fast-paced, transactional Property & Casualty (P&C) sales. Your mission is to scale closing ratios and ensure the team consistently crushes its monthly revenue targets.

Key Responsibilities
  • Team Leadership & Performance: Manage, mentor, and scale a high-volume team of licensed Insurance Account Executives (AEs) to meet and exceed monthly quotas.
  • Deal Coaching & Conversion: Conduct regular 1-on-1s, call shadowings, and script breakdowns. Train the team on consultative sales techniques, value-based selling, and advanced objection handling.
  • Pipeline & Metric Management: Closely track day-to-day metrics (close rates, talk time, average policy value, speed-to-lead) to spot bottlenecks and ensure efficient lead routing and execution.
  • Cross-Functional Alignment: Work hand-in-hand with our SDR Manager and Marketing teams to calibrate lead quality, streamline high-velocity handoffs, and feedback loop data.
  • Compliance & Product Mastery: Keep the team up to speed on current underwriting guidelines, multi-carrier platform updates, and compliance standards across different states.
  • Culture Carrier: Drive a competitive, collaborative, and high-accountability environment where agents are excited to win together.

Requirements

What We're Looking For
  • Experience: 3+ years of sales leadership experience, preferably managing inside sales or high-velocity closing teams within tech, insurtech, or a progressive brokerage environment.
  • Insurance Foundation: Active Property & Casualty (P&C) or General Lines insurance license is highly preferred. Deep comfort navigating insurance underwriting, quoting, and binding workflows is a must.
  • Data-Driven Mindset: You manage by numbers, not just feelings. Experienced with modern sales tools (CRM/dialers like Close.ai, Salesforce, or HubSpot).
  • Consultative Sales Mastery: You know how to coach a team to explain complex coverage options, policy terms, and value props in simple, straight-talk language-leaving out the dry insurance jargon.
  • Startup Agility: You thrive in fast-paced, fluid environments where processes evolve quickly as the company scales.
  • Location: Ability to work out of our Austin, TX, or San Francisco, CA, according to company hybrid guidelines.

Benefits

Why You'll Love Working Here
  • Growth Opportunity: Join a company in its early stages and help build its foundation for success.
  • Competitive Compensation: Receive a competitive salary with uncapped commissions.
  • Equity: Opportunity to earn equity compensation.
  • Comprehensive Benefits: We offer a full health and welfare benefits package, a 401(k) match, and flexible Paid Time Off.
  • Fun Office Atmosphere: Lively office, stocked with endless snacks, regular Happy Hours, catered lunches, and team building events.
  • Work-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure.


Compensation & Schedule
  • Base Salary: The base salary for this position is $75,000, with an On-Target Earnings (OTE) of $150,000.
  • Commission: Uncapped commission and regular SPIFFs.
  • Schedule: This is a full-time office position.

About Outdoorsy

Outdoorsy is a peer-to-peer recreational vehicle (RV) rental marketplace. The company was founded in 2015 by Jeff Cavins and Jennifer Young. Outdoorsy allows RV owners to rent out their vehicles to travelers, and it offers a wide range of RVs, including motorhomes, campervans, and travel trailers. The company is headquartered in San Francisco, California, and it has more than 200 employees. Outdoorsy has raised more than $80 million in funding from investors such as Aviva Ventures, Altos Ventures, and Tandem Capital.
Learn more about Outdoorsy
Size
200 employees
Industry
Hospitality & Recreation
Founded
2014
* Ladders Estimates

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