Greybull Stewardship

Courtroom Connect President, CVN Courtroom Connect, founded in 2001, develops technology solutions and online platforms for legal professionals. The company operates two primary brands: Courtroom View Network (CVN) and Remote Counsel. CVN provides live and on‑demand access to courtroom proceedings and leverages a substantial archive of civil trial video to power a professional subscription service. Position Summary Courtroom Connect seeks a President, CVN to lead the next phase of CVN’s growth. The President holds full P&L accountability and strategic autonomy across Product, Design, Sales, and Marketing, with a mandate to transform a premier archive of civil trial video into a scaled, high‑growth subscription franchise for the legal community. Mandate 1) Product Strategy & Design - Own the end‑to‑end subscriber experience for a professional video library, ensuring discovery, viewing, and purchasing journeys are intuitive, efficient, and habit‑forming for attorneys, litigation support professionals, and academic users. - Define the information architecture and metadata strategy (e.g., jurisdiction, judge, practice area, procedural phase) to enable precise search, filtering, and browsing. - Establish curation and packaging models (collections, series, next‑best‑watch, alerting) that surface the most relevant trials and increase recurring engagement and renewal. - Champion a professional‑grade video experience (captions, chapters, transcript sync, timestamped bookmarks, resume‑watch, accessibility), optimized for long‑form professional use. - Simplify commerce and identity flows for individuals and firms—including trials, checkout, upgrades/downgrades, renewals, seat management, and SSO—to reduce friction and increase conversion and LTV. - Create a design system and experimentation discipline across surfaces (web, mobile, player, email), with instrumentation and A/B testing that deliver measurable improvements on a predictable cadence. 2) Revenue Growth & Market Expansion - Architect a metrics‑driven commercial engine that consistently expands individual and firm subscriptions, with clear ownership of new MRR, renewal rate, and LTV. - Build high‑leverage sales coverage, compensation architecture, pipeline management, and rigorous forecasting to deliver predictable growth. 3) Operational Leadership - Allocate resources to the highest‑return initiatives, remove execution bottlenecks, and drive disciplined operating mechanisms without requiring CEO intervention. Candidate Profile Experience - 7–10+ years of executive leadership with a strong emphasis on subscription revenue growth; demonstrable success scaling SaaS or content subscriptions. - Proven ability to build and lead sales organizations that exceed aggressive growth targets; expertise in pipeline development, compensation design, and KPI‑driven performance management. - Experience with content licensing or digital asset distribution is strongly encouraged. - Successful leadership of high‑output remote or hybrid teams. Capabilities - Depth in product design for content libraries: information architecture, curation, search/filter UX, and professional‑grade video experiences. - Fluency in commerce and identity for subscriptions (trials, entitlements, renewals, SSO) and in running disciplined experimentation programs. - Ability to architect a scientific, metrics‑driven revenue engine; mastery of forecasting, cohort analysis, and LTV/CAC economics. - Executive range to operate from strategic P&L leadership to hands‑on customer and product work. Location and Work Arrangement This role may be performed in a remote or hybrid environment; periodic travel may be required for team leadership and key customer engagements. Application and Nomination Review of applications will begin immediately and continue until the position is filled. To apply, please email a position‑specific cover letter and résumé to Jennifer N. Hiatt at jennifer@greybullstewardship.com. Nominations may be emailed to the same address. Applicants requiring reasonable accommodation to participate in the process should contact Jennifer N. Hiatt at 307‑249‑1161.

Company Overview VSSTA is an automotive technology company transforming how collision centers and repair shops perform ADAS calibrations. Founded in 2020 and backed by private equity, VSSTA enables customers to bring calibration services in-house through a combination of proprietary software, remote capabilities, and integrated hardware while unlocking new revenue, improving cycle times, and reducing reliance on third-party providers. VSSTA operates at the intersection of automotive repair, SaaS, and connected hardware, serving a rapidly expanding market driven by vehicle complexity and safety requirements. As the industry evolves, VSSTA is positioned as a critical partner to collision centers seeking to modernize operations and capture high-margin calibration revenue. Position Summary VSSTA is seeking a highly hands-on Vice President of Sales to lead all new business revenue across direct and partner-driven channels. This leader will: - Build structure and accountability across the sales organization - Drive consistent pipeline generation and forecast accuracy - Scale a repeatable, metrics-driven sales motion - Partner closely with Marketing and Partnerships to maximize demand generation The VP of Sales will report directly to the CEO and play a central role in defining how VSSTA scales. Why This Role Is Critical Now VSSTA is transitioning from early-stage growth to scalable revenue execution. The company has strong market demand and a differentiated offering but requires a sales leader to: - Build pipeline discipline and consistency - Improve forecast accuracy and visibility - Build and develop a high performing sales team - Increase conversion rates and reduce sales cycle variability - Successfully integrate partner-driven pipeline into sales execution - Create a scalable foundation for continued growth This role will define the next phase of growth by turning sales into a predictable, high-performing revenue engine. Key Responsibilities Revenue Leadership (Player-Coach) - Personally develop and close strategic opportunities - Carry and exceed an individual quota - Lead from the front across the full sales cycle - Execute consultative sales motions with collision centers, MSOs, and automotive service providers Sales Team Leadership & Development - Recruit, onboard, and develop high-performing sales talent - Establish clear expectations for pipeline, conversion, and bookings - Conduct rigorous pipeline reviews and deal inspections - Coach on discovery, qualification, , and closing strategy - Build the organizational structure required to scale Channel & Partner Revenue Development - Work closely with the Partnerships leader to convert partner-driven demand into revenue - Ensure alignment between partner pipeline and field execution - Establish accountability for partner-sourced pipeline and conversion - Build a scalable model for partner-driven growth Sales Process, Forecasting & Infrastructure - Own and continuously improve the end-to-end sales process - Drive disciplined CRM usage and pipeline hygiene - Build accurate forecasting models and pipeline coverage models - Partner with Finance on revenue planning and performance tracking - Implement structured sales methodologies and inspection frameworks Go-To-Market Execution - Partner with Marketing on messaging, campaigns, and sales enablement - Provide structured market feedback on pricing, packaging, and competitive positioning - Identify expansion opportunities across markets and segments, - Collaborate with Operations and Customer Success to ensure successful onboarding and adoption Qualifications & Experience - 8–15 years of professional sales experience, including 3–5+ years in a formal leadership role - Experience in B2B SaaS, automotive technology, and/or selling into collision repair and automotive service environments - Proven success as a quota-carrying sales leader (player-coach) - Track record of building structure, process, and accountability in a scaling organization - Experience managing both direct sales and partner/channel-driven revenue models - Strong CRM discipline and data-driven management approach (HubSpot preferred) - Comfortable operating in a private equity-backed, high-accountability environment Core Leadership Traits - Hands-on, player-coach leadership style - Strong coaching and team development capability - Operational mindset with a focus on building repeatable systems - Disciplined approach to forecasting and pipeline management - High credibility with customers, partners, and executive leadership - Bias toward execution, accountability, and measurable results Location & Travel This role is fully remote within the United States. Regular travel is required for customer engagements, field sales support, partner development, and industry events. Compensation This is a full-time, exempt position with an OTE of $250,000+. Salary and discretionary bonus commensurate with experience, plus medical insurance and PTO. To Apply Please submit your application via LinkedIn (preferred), or send your resume and a brief note outlining relevant experience to jennifer@greybullstewardship.com. Equal Opportunity Employer VSSTA is proud to be an equal opportunity employer. All applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, veteran status, genetics, disability, or age.

Role Description The Vice President, Finance & Accounting will serve as the senior-most financial leader at VSSTA, reporting directly to the CEO and working closely with the Greybull Stewardship team. This role is responsible for leading all accounting, finance, and reporting functions while building scalable processes, improving cash predictability, and providing strategic financial insight to support growth. This is a hands-on, player-coach role ideal for a finance leader with experience in PE-backed, subscription-based or technology-enabled services businesses. Key Responsibilities - Financial Leadership & Strategy - Partner with the CEO on strategic planning, OGSM execution, and capital allocation decisions - Translate company strategy into financial plans, forecasts, and operating KPIs - Provide clear visibility into normalized EBITDA, cash flow, and unit economics - Support board reporting, investor materials, and Greybull operating cadence - Accounting & Close - Own monthly, quarterly, and annual close processes with a target 5-business-day close - Ensure accurate GAAP-compliant financial statements (P&L, Balance Sheet, Cash Flow) - Manage revenue recognition for subscription and service-based offerings - Oversee external accounting firms, auditors, and tax advisors - Cash Flow & Working Capital - Build and maintain a rolling 13-week cash forecast - Actively manage accounts receivable, payables, and collections - Oversee sales tax compliance and multi-state reporting - Establish cash management policies and controls - Planning, Forecasting & Analytics - Lead annual budgeting and rolling forecast processes - Develop financial models tied to ARR growth, sales pipeline, and support capacity - Build dashboards tracking ARR, churn, gross margin, cash runway, and operating leverage - Provide actionable insights to functional leaders - Systems & Process Improvement - Own financial systems and reporting tools (billing, CRM integrations) - Improve billing accuracy, collections cadence, and financial controls - Drive process automation and scalability across finance operations Qualifications - Eight years of progressive finance and accounting experience - Prior experience in a PE-backed, SaaS, or technology-enabled services company - Strong accounting foundation; CPA preferred - Experience building or scaling finance functions - Highly analytical, detail-oriented, and operationally minded - Strong communicator with high emotional intelligence What Success Looks Like (First 12 Months) - Predictable monthly close and trusted financial reporting - Clear visibility into cash flow and operating performance - Reduced financial volatility through forecasting discipline - Finance viewed as a strategic partner across the organization Location/Salary This role is remote-friendly within the United States, with periodic travel as needed. Priority will be given to candidates living in south Texas. The salary is listed at $150K-$165K. Application and Nomination Review of applications will begin immediately and will continue until the position is filled. To apply for this position, please email a position-specific cover letter and resume to Jennifer N. Hiatt at jennifer@greybullstewardship.com. Nominations may be emailed to the same email address. Applicants needing reasonable accommodations to participate in the applications process should contact Jennifer N. Hiatt directly.