Hybrid
Remote
Financial
himalayas
About this role
OTE Range: $110,000 - $150,000About Roamly Roamly Insurance Group (Roamly), a wholly-owned subsidiary of Outdoorsy Holdings, Inc., is the first full-stack Insurtech for travel enthusiasts. Roamly is where the insurance industry and technology intersect to enhance the customer experience.
As a disruptor in the specialty insurance space, Roamly removes traditional technology and coverage barriers by providing innovative protection for underserved markets across recreation lines and global mobility markets. For more information, visit roamly.com.
About the RoleAs an Insurance Account Executive at Roamly, you will be a front-line hero for our adventurous community. You will serve as a trusted advisor, assisting both prospective and existing clients in obtaining insurance coverage for homeowners, auto, RV, and various other products. With uncapped com
missions and amazing Front Line Leaders to support you throughout your onboarding and beyond, you are truly set up to absolutely crush your OTE and grow your career!
Key
ResponsibilitiesCustomer Engagement & Consultative Sales Engage customers using a consultative sales approach to understand their insurance needs and recommend personalized solutions across property, casualty, and personal lines.
Proactively identify opportunities for cross-selling and up-selling, and assist customers in transitioning between Roamly and third-party insurance carriers when appropriate. Clearly explain coverage options, policy terms, and insurance processes in a way that’s easy for customers to understand.
Lead Conversion & Sales Execution Drive lead conversion through high-volume outbound outreach and responsive handling of inbound inquiries. Manage the complete sales process—from quoting insurance products using Roamly’s proprietary tools, to gathering underwriting information, and guiding customers through to policy purchase and binding.
Tools, Documentation & Compliance Maintain accurate and timely documentation of customer inter
Tools & Tech Stack
Commission Structure
Base Salary
Not disclosed — ask in interview
Commission
Uncapped
OTE
$150k (range: $40k–$150k)
Ramp Period
Not mentioned — clarify timeline
Selling Motion
Prospecting
Hybrid
Mix of inbound leads and outbound prospecting
Buyer Persona
C-Suite
Selling to executive decision-makers
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
No ceiling on earnings
Financial Services — Interview Intel
Typical Sales Cycle
3–6 months (Retail) · 6–18 months (Institutional)
Common Buyer Objections
- "Regulatory concerns — need compliance approval"
- "We already have a vendor for this"
- "Need to see 3-year track record"
- "Committee-based decision — multiple approvers"
Key Industry Metrics
Hot Topics to Reference
- • AI in fraud detection and compliance
- • Open banking APIs
- • ESG investing mandate shifts
- • Embedded finance partnerships
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionAs an Account Executive with Roamly, you'll own the entire revenue pipeline and be measured on quota attainment.
Trust-building is paramount — prospects need confidence in your expertise.
This remote-friendly role provides geographic flexibility while maintaining access to a financial services market.
The compensation range of $40k–$150k OTE suggests a competitive package for this market segment.
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