Regional Vice President - Sales

Trustpoint.One; Northern (KY); Hybrid; USD 125,000 - 175,000; Full time

Job summary

Trustpoint.One, a leading ALSP delivering legal consulting, staffing, outsourcing and eDiscovery, seeks a Regional Vice President - Sales to drive pipeline growth and high‑value deals across the U.S. remotely, reporting to the CRO and guiding a team of ~10 sales reps.

You will partner with the CRO and Marketing to refine the GTM strategy, coach executives, and craft compelling client pitches, leveraging SME support to close long-cycle, multi‑million opportunities while traveling up to 50% as

Qualifications

• 7+ years in legal services, consulting, or professional services targeting enterprise clients.
• Proven track record of managing five or more direct reports.
• Experience with long-cycle, high-value sales (3–6 months, $100K–$1M+ deals).
• Bachelor’s degree required; MBA or JD a plus.

Responsibilities

• Lead and mentor 10+ direct reports; conduct weekly 1:1s.
• Coach AEs with SMEs; join high-stakes client meetings.
• Partner with CRO and Marketing to refine GTM; design training and incentives.

Skills

Leadership

Coaching

Strategic thinking

Communication

Account-based selling

Education

Bachelor’s degree

MBA or JD a plus

Job description

Trustpoint.One is a leading alternative legal service provider (ALSP) delivering innovative legal consulting, staffing, and outsourcing solutions to AmLaw 200 law firms and Fortune 500 companies. Our mission is to drive efficiency, compliance, and value for clients through tailored services and cutting-edge technology.

With a 30-person sales team supported by subject matter experts (SMEs), we are reorganizing to enhance agility and growth under a new Chief Revenue Officer (CRO).

Title: Regional Vice President - Sales
Location: Remote (U.S.)
Reports to: Chief Revenue Officer (CRO)
Direct Reports: Approximately 10 seasoned sales representatives
Department: Sales
Type: Full-Time

With a focus on strategic management and subject matter expertise, the Regional Vice President partners with experienced salespeople to ensure effective client engagement. This requires strong knowledge and working experience of our service portfolio (legal consulting, staffing, outsourcing, and eDiscovery) to guide pitches and join high-stakes deals, while prioritizing pipeline growth, deal progression, and team accountability.

Team Leadership and Coaching (60%)

• Manage and mentor 10+ direct reports, fostering collaboration and accountability.
• Conduct weekly 1:1s to discuss account penetration and expansion.
• Upskill non- President's Club members to diversify revenue (target: 25% increase in non- President's Club members).
• Implement account-based selling (ABS) strategies, coordinating with SMEs to map client stakeholders (e.g., GCs, legal ops, related parties).

Service Knowledge and Deal Support (20%)

• Maintain strong knowledge of legal consulting, staffing, and outsourcing services to coach AEs on effective positioning and cross-selling.
• Author quarterly articles or white papers to position yourself and Trustpoint.One as subject matter experts.
• Create two CLE presentations per year to assist sales reps in providing value to prospects.
• Join high-stakes client meetings to reinforce credibility and strategy.
• Collaborate with SMEs when necessary to ensure pitches and demos align with client needs.

Strategy and Alignment (20%)

• Partner with CRO and Marketing to refine our go-to-market (GTM) strategy and develop innovative marketing initiatives.
• Provide input on sales playbooks, training, and incentives to drive team performance.
• Uncover networking and speaking opportunities for yourself and your team.

Experience

7+ years in legal services, consulting, or professional services targeting enterprise clients in a delivery capacity.

Proven track record of managing five or more direct reports.

Experience with long-cycle, high-value sales (3-6 months, $100K-$1M+ deals).

Skills

Strong coaching and leadership skills to manage seasoned employees and foster collaboration.

Working knowledge of legal consulting, staffing, eDiscovery, and/or outsourcing to guide pitches, with the ability to leverage SMEs for technical expertise outside your own scope.

Excellent communication and strategic thinking to align with CRO and navigate complex client organizations.

Education

• A bachelor’s degree is required.
• MBA or JD a plus but not required.

Attributes

• Collaborative and able to work with SMEs and cross-functional teams to deliver client value.
• Adaptable to a reorganized sales structure and comfortable managing change.
• Comfortable ideating and executing innovative marketing efforts, including social media and AI-driven strategies.
• Willingness to travel up to 50% of the time

Base Salary: $125,000-$175,000
Incentives: Performance-based bonus (25-50%)
Benefits: Health, Dental, 401(k), market competitive PTO