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Role Description

We're hiring our first dedicated Account Executive to drive expansion and growth. This is a foundational role on our small and mighty team—you'll have the opportunity to shape how we serve our customer base, and all future customers, from the ground up.

This isn't a typical sales role. You won't be making 100 cold calls a day or running aggressive outbound campaigns. Instead, you'll be building relationships within a tight-knit professional community, attending industry conferences, understanding complex workflows, and positioning Certificate of Service as the operational partner that makes our legal customer’s lives easier.

What You'll Do

• Build relationships that matter
• Attend legal conferences and regional bankruptcy events to connect with trustees and legal practitioners face-to-face
• Cultivate referral relationships with trustees, attorneys, and bankruptcy software vendors
• Become a trusted advisor and key part of the community
• Drive strategic account acquisition
• Execute an account-based sales motion for high-value trustee prospects
• Orchestrate demos that showcase how our platform solves real operational challenges
• Navigate complex buying processes involving trustees, office managers, and IT staff
• Collaborate with our leadership team to close deals and onboard new clients successfully
• Become a subject matter expert
• Master the intricacies of legal, bankruptcy administration, and trustee workflows
• Understand how our platform integrates with case management systems
• Learn the competitive landscape and articulate our clear value proposition
• Stay current on industry trends, regulatory changes, and market dynamics
• Lay the foundation for scale
• Document what works (and what doesn't) as we build our sales playbook
• Provide feedback to product and marketing teams based on customer conversations
• Help establish sales processes, CRM workflows, and success metrics
• Contribute to our broader go-to-market strategy as the voice of the trustee customer

Qualifications

• Industry expertise: If you haven’t worked in and around legal and bankruptcy markets, you must be willing to jump into the deep end and learn the ecosystem and credibly speak the language.
• Intellectual curiosity: You ask great questions, dig deep to understand problems, and genuinely enjoy learning new things. You're energized by the challenge of becoming an expert in a new domain.
• Optimism and resilience: You believe in what you're selling. You stay positive. You look to grow from your mistakes (we all make them!)
• Willingness to travel: Approx 40% - 50% travel is required, primarily to bankruptcy conferences and in-person client meetings.
• Ability to flex into US timezones, with ability to meet with company leadership and team members on PST

Requirements

• Proven sales ability: You've successfully sold B2B products or services, ideally in a relationship-driven, high-touch environment. You know how to build pipeline, manage complex sales cycles, and close deals. If you don’t come with this, but are willing to learn, that’s a great place to start.
• Experience shepherding deals through a sales funnel in a CRM
• Familiarity with bankruptcy case management software (BSS, Best Case, Epiq, NextChapter, etc.)
• Background in legal services, court administration, or bankruptcy

Benefits

• Substantial earning potential
• Competitive base salary with uncapped commission structure
• Accelerators for exceeding quota
• Long-term incentive opportunities as the business grows
• Ownership and impact
• Be the first AE hire—shape the role, build the playbook, and establish best practices
• Partnership with the CEO and leadership team
• Real influence over product roadmap and go-to-market strategy
• Clear path to leadership as we scale
• Professional growth
• Deep domain expertise in a specialized, stable market (bankruptcy noticing is federally mandated and non-discretionary)
• Backed by Bristlecone Companies' operating resources and expertise
• Mentorship from experienced PE operating partners
• Opportunity to master consultative, relationship-based sales
• Quality of life
• Remote-first culture with flexibility to work from anywhere (travel requirement notwithstanding)
• Collaborative, low-ego team that values continuous improvement
• Mission-driven work: we help legal professionals serve people in financial distress more effectively