Sales Development Representative (SDR) Manager

Job Description

Job Description

About 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 Role

As our SDR Manager , your primary mission is to build, scale, and optimize a predictable, repeatable outbound pipeline engine.

While you are based in Austin or San Francisco, your daily focus will be on managing and scaling our high-performing offshore SDR team. We need a leader who has "been in the trenches" as an SDR, loves looking at data to fix pipeline bottlenecks, and knows how to drive performance across international time zones.

Key Responsibilities

• Lead & Mentor: Manage, coach, and develop a high-performing team of offshore SDRs to consistently hit and exceed monthly pipeline goals.
• Optimize Offshore Operations: Act as the strategic partner and daily manager for our offshore SDR team—ensuring alignment on messaging, quality control, data accuracy, and performance metrics.
• Build the Playbook: Refine outbound sequencing, email copy, cold calling scripts, and objection-handling strategies specific to Roamly’s target insurance markets.
• Data-Driven Execution: Monitor, analyze, and report on key performance indicators (KPIs) including call volumes, email conversion rates, meetings booked, and pipeline generated.
• Tech Stack Champion: Oversee daily utilization of our sales engagement tools (Close.io, Tableau, etc.) to ensure maximum efficiency.
• Cross-Functional Collaboration: Partner closely with Marketing and Account Executives to ensure seamless lead handoff and tightly aligned target account strategies.

Requirements

What We're Looking For

• Experience: 2+ years of direct experience managing a Sales Development or Business Development team, ideally within a high-growth tech, SaaS, or insurtech environment.
• Global Team Management: Proven experience managing, training, or scaling offshore SDR teams is a major plus. You understand the nuances of managing remote, cross-cultural, and asynchronous team workflows.
• SDR Mastery: You have "been there, done that" as a top-performing individual contributor SDR earlier in your career. You know how to source a lead, book a meeting, and handle tough objections.
• Process & Analytics Mindset: You love data and use it to spot trends, diagnose pipeline bottlenecks, and coach reps on specific areas of improvement.
• Coach Mentality: Passionate about career development. You take pride in turning entry-level reps into future enterprise sales leaders.
• Location Requirement: Must be located in Austin, Texas, or San Francisco, CA, and work from the office full-time.

Benefits

Why You'll Love Working Here

• Growth Opportunity: Join a company in its early stages and help build its foundation for success.
• 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

• Competitive Compensation: Receive a competitive salary with uncapped commissions and regular SPIFFs.
• Schedule: This is a full-time office position.