About Self Bill Pro

Self Bill Pro is a rapidly growing startup dedicated to solving one of the most persistent challenges in the employee benefits ecosystem: the complexity of monthly benefits billing. We provide a technology-enabled service where our dedicated team leverages proprietary software to eliminate the administrative burdens of manual invoice audits and costly errors. Our mission is to streamline this critical operation, freeing up employers, brokers, and carriers to focus on their strategic priorities and better serve their people.

Job Summary

The Sales Manager is one of Self Bill Pro's most important hires in 2026. This is the organizational glue of our go-to-market engine — the person who keeps our sales and marketing operation running with precision and energy every single day, freeing our CEO to focus on the high-level strategic relationships and new business origination that drive our growth. You will manage a team of Account Executives and work alongside our Sales and Marketing Operations Manager and external BDR. You will own pipeline visibility, sales process discipline, and team accountability. Over time, as you grow into the role, you will begin to represent Self Bill Pro externally — attending carrier sales events, building relationships with carrier reps, regional sales managers, and insurance brokers, and eventually becoming a true field presence alongside our CEO. This is a rare opportunity to join a company at an inflection point, learn a highly specialized GTM motion from a founder who built it from scratch, and grow into a senior sales leadership role as the business scales.

Key Responsibilities

Team Leadership & Deal Coaching:Manage and develop our Account Executive team, including pipeline reviews, deal coaching, follow-up accountability, and proactive performance development.
GTM Collaboration:Work daily alongside our Sales & Marketing Operations Manager to direct outreach priorities, campaign execution, and marketing activities across our three key GTM audiences: strategic insurance carrier relationships, prospective carriers, and brokers.
Outbound Pipeline Management:Direct and prioritize the work of our external BDR, who runs our outbound prospecting infrastructure.
CRM & Process Discipline:Own CRM hygiene and pipeline visibility — ensure every active deal, carrier relationship, and outreach thread is meticulously documented and actively moving forward.
Founder Shadowing: Attend carrier and broker conversations alongside the CEO — both virtually and in person — building a deep command of our relationship-selling motion and becoming a true strategic partner in how we go to market.
Field Penetration:Gradually build your own relationships with carrier sales reps and regional sales managers across our carrier network, deepening the field-level penetration that turns relationships into consistent deal flow.
First Line of Defense:Serve as the day-to-day point of escalation for the sales team.
What Success Looks Like
At 90 Days:
You have a complete, organized view of our active carrier relationships and pipeline, and the team has a reliable system for keeping it current. You've established yourself as the dedicated manager for the rest of the sales team — running weekly pipeline reviews, ensuring nothing falls through the cracks, and sitting in on enough carrier and broker conversations to articulate our value proposition confidently.
At 12 Months:
The day-to-day sales and marketing engine runs smoothly without the CEO in the room. You are beginning to show up in carrier field relationships — attending regional sales meetings, following up with reps, and becoming a highly recognizable face of Self Bill Pro in the field. The CEO's time is freed up for new relationship origination and high-level strategy.
Growth Path
Self Bill Pro is at an inflection point. Our industry footprint and brand awareness is expanding rapidly, and the person who joins now will grow alongside that expansion. The Sales Manager role is intentionally designed as a launchpad — the expectation is that as new strategic relationships come online and the sales organization scales, this person grows into a VP of Sales or equivalent senior leadership role. We are investing in the right person for the long term.

Qualifications

Industry Experience:5+ years of experience in a sales role within employee benefits, group insurance, HR technology, benefits administration, or a closely adjacent field. Direct industry experience is strongly preferred.
Closing Track Record:Formal sales training and real closing experience — you have carried a quota, successfully managed a pipeline, and won complex deals through relationship-building, not just order-taking.
Leadership Instincts:5+ years of experience managing and coaching other salespeople, with a track record of making the people around them better.
Flawless Execution:Exceptional organizational discipline; you are the kind of person who naturally builds systems and never lets a follow-up fall through the cracks.
Channel-Sales Mindset:Natural relationship builder who understands that our business is built on trust, not transactional sales. Comfort with long sales cycles and channel-dependent, partner-driven selling is critical.
Travel Availability: Ability to travel regularly to Ambler, PA to work alongside our CEO, especially in the early months of the role. Approximately 25% travel expectation. While this position is remote, in-person collaboration will be expected for onboarding, key meetings, and ongoing strategic alignment.
Ambition:You are not looking for a comfortable, static job — you are looking for a true platform to build a department and grow your career.

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