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Business Development Manager

$80k - $120k

Squaremouth Inc

Business Development Manager For Broker Partnerships

Proper Insurance is the national leader in short-term rental (STR) insurance, with over 200,000 policies written across all 50 states. As a Coverholder at Lloyd's of London and the endorsed insurance provider for Vrbo, we offer vacation rental owners a single, comprehensive policy covering both commercial and personal use, a solution that traditional carriers simply cannot match.

Founded in 2014 and headquartered in Bozeman, MT, we have grown from a two-person operation to a team of 100+ and continue to expand at an accelerated pace. Recently acquired by Specialty Program Group (SPG), Proper is now part of a broader portfolio with expanded distribution opportunities and resources to scale our broker/agency channel nationwide.

The short-term rental market is one of the fastest-growing segments in hospitality and real estate, and Proper Insurance sits at the center of it.

The Opportunity

This is a newly created role and a foundational one. As Proper's first dedicated Business Development Manager for Broker Partnerships, you will own the activation, development, and ongoing management of our independent insurance agent channel. While our direct-to-consumer and property manager channels are well-established, our broker network represents a significant untapped growth opportunity.

You will inherit an established foundation: 1,200+ appointed agencies already in our system and 200+ pending appointment applications ready to be handed off to you for cultivation. Your primary mission is to transform this base from dormant to actively producing, while simultaneously cultivating new broker relationships and leveraging strategic partnerships developed through our recent acquisition.

You will be based out of our Bozeman MT headquarters and work directly with the Chief Sales Officer to build, train, and support a national network of independent agents who view Proper as their go-to STR carrier. The relationships you develop and the systems you build will establish a repeatable broker engagement model that scales alongside the company.

This is not a role for someone looking for a defined playbook. It is an opportunity for a motivated, relationship-driven professional to build something from the ground up in a specialty market that most agents have never encountered.

Compensation & Benefits

Base Salary: $80,000 – $120,000 (depending on experience)

Performance Bonus: Up to $80,000 annually, structured in tiers tied to broker channel net revenue growth

Total Maximum Compensation: $200,000

Travel: Limited but expected (10-15% annually) for key broker visits, industry events, and strategic partner meetings

Additional benefits include:

  • Comprehensive health, dental, vision, and life insurance
  • HSA, FSA, and HRA options
  • Short-term disability coverage
  • 401(k) retirement plan
  • Flexible PTO, sick days, and all major holidays off
Responsibilities
Appointment Processing & Onboarding
  • Process and vet pending broker appointment applications currently in queue
  • Conduct thorough vetting of new agency applications using established criteria (E&O coverage, licensing, book composition, producer experience)
  • Execute appointment agreements and ensure all compliance requirements are met
  • Onboard newly appointed agencies with product training, quoting systems, and underwriting guidelines
Relationship Cultivation & Reengagement
  • Reactivate and nurture relationships with 1,200+ existing appointed agencies, many of which have gone dormant or produce inconsistently
  • Conduct regular business reviews with active and semi-active agencies to identify barriers to production and provide support
  • Develop targeted outreach campaigns to reengage agencies that have written business previously but have since gone inactive
  • Build co-marketing materials, email campaigns, and education resources to keep Proper top-of-mind with appointed agents
New Broker Prospecting & Development
  • Identify and prospect high-potential independent agencies and regional brokerages with exposure to STR property owners
  • Leverage strategic relationships (including those developed through our recent acquisition) to access new broker networks and distribution channels
  • Develop and execute outreach strategies for agencies in high-STR-concentration markets (mountain resort towns, beach communities, metropolitan short-term rental hubs)
  • Coordinate with the CSO on activating partnership opportunities across the broader SPG network
Training & Enablement
  • Deliver ongoing product training to new and existing appointed agencies (webinars, one-on-one calls, written resources)
  • Ensure agents understand Proper's unique value proposition in the STR space and can effectively position our coverage vs. traditional carriers
  • Provide agencies with underwriting guidance, common objections/rebuttals, competitive positioning, and claims examples
  • Develop standardized training materials and resources that scale as the broker network grows
Performance Tracking & Reporting
  • Monitor agency-level KPIs including gross written premium (GWP), close ratios, policy count, and renewal retention
  • Identify top-performing agencies and replicate their success across the network
  • Flag underperforming agencies for additional support or potential termination
  • Report monthly on partnership pipeline metrics, new appointments, reactivations, and channel revenue growth
  • Maintain accurate records in CRM of all agency interactions, training sessions, and performance data
Lead Coordination
  • Manage inbound broker-referred leads and ensure proper routing to internal sales team or back to originating agent
  • Track lead-to-close conversion by agency to identify high-value partnerships
  • Coordinate with sales operations to ensure broker-sourced business is properly attributed and compensated
Qualifications
Required:
  • 3+ years of experience in business development, broker relations, or agency management within the insurance industry
  • Proven ability to manage a book of broker/agency relationships with measurable production outcomes
  • Strong understanding of insurance distribution models (retail agents, MGAs, wholesalers).
  • Excellent communicator with the ability to train agents on complex products and position specialized coverage
  • Self-directed and process-oriented—comfortable building systems and structure in an emerging channel
  • Proficiency with CRM platforms (Salesforce, HubSpot, or similar) and strong organizational discipline for managing high-volume outreach and follow-up
  • Property & Casualty Insurance License preferred. If not currently licensed, Proper will support obtaining your P&C license as part of onboarding.
Preferred:
  • Experience working with MGAs, program administrators, or specialty lines carriers
  • Familiarity with the short-term rental market, hospitality insurance, or property/casualty products for real estate investors
  • Existing relationships with independent agencies or regional broker networks
  • Track record of building a broker channel from early stage to scaled production
Differentiators:
  • Prior experience working in insurance or similar field (understanding E&O requirements, licensing verification, compliance standards)
  • Demonstrated success reactivating dormant client/partner relationships or improving production from underperforming partners
  • Background in training or enablement roles (creating training resources, delivering webinars, developing playbooks)
  • Comfort operating in a specialty/niche market vs. traditional P&C distribution
Who Thrives Here

Our most successful team members are energized by ownership—people who see a gap and move to close it without waiting to be asked. The BDM role is purpose-built for someone who genuinely enjoys the relationship-building aspect of sales, takes pride in developing expertise in a niche market, and is motivated by the long-term compounding value of a well-cultivated broker network.

You will be joining a fast-moving company in a market that is still defining itself—and doing so as part of a broader organization (SPG) with expanded resources and strategic relationships that open doors. If you are someone who finds more energy in building something new than in managing something established, and if the idea of being the first person to own a channel excites you rather than intimidates you, this role is worth a serious conversation.

Vacancy posted 5 days ago
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