Now Hiring - Legacy Paint Holdings - Professional Services Sales Lead in Pittsburgh, PA

Full description of the position

Sales Lead - Financial Services for Contractors Legacy Paint Holdings is expanding its financial services arm that provides bookkeeping, financial reporting, and operational clarity to contractors across the US. We are hiring a Sales Lead to own the sales function and help scale this division intentionally and profitably. This is a full-cycle, relationship-driven sales role. You'll be speaking directly with business owners about their books, margins, cash flow, and financial blind spots - and helping them move toward clarity and control. This is not transactional sales. This is not a side hustle. This is a role for someone who takes ownership. Role Overview The Sales Lead will be responsible for managing the entire sales process - from first contract through close - for recurring monthly financial services. You'll work closely with leadership to refine messaging, improve conversion, and build repeatable systems as the division grows. This role is results-driven, not clock-driven, but most successful candidates work 40-55 hours per week, especially during the first 90 days. Key Responsibilities * Own the full sales cycle: discovery, qualification, proposal, follow-up, and close * Speak confidently with contractors about bookkeeping, financial reporting, and margins * Qualify prospects and ensure alignment on scope, expectations, and pricing * Close recurring monthly service agreements * Maintain disciplined follow-up and pipeline management * Log activity and deal progression in CRM * Provide feedback to leadership on objections, pricing, and market demand * Help shape sales processes, scripts, and follow-up cadence as the division scales Ideal Candidate Profile This role is a strong fit if you: * Have experience in sales, preferably in services, B2B, or financial-related fields * Are comfortable selling trust-based, recurring services * Can hold confident conversations with business owners * Are organized, disciplined, and consistent with follow-up * Take ownership of outcomes, not just activity * Want growth, responsibility, and long-term upside Experience with contractors, bookkeeping, accounting, or financial services is a plus, but nor required if you're sharp, coachable, or motivated. Compensation * $80,000-$140,000+ annually, including commissions * Clear path to exceed six figures * Opportunity to grow into a Head of Sales / Division Lead role as the business scales Time Commitment * Full-time, results-driven role * 40-55 hours per week expected * Early ramp period may require higher effort to build pipeline momentum Why Legacy Paint Holdings * You're selling services that genuinely help contractors run better businesses * Backed by real operators, not theory * Financial services are a priority growth arm of the company * Opportunity to build systems, not just hit quotas * Long-term leadership upside for the right person Pay: $40.00 - $70.00 per hour Expected hours: 40.0 - 55.0 per week Benefits: * Cell phone reimbursement * Flexible schedule * Opportunities for advancement * Travel reimbursement * Work from home Application Question(s): * Why does this role specifically interest you? * Describe your experience selling recurring or service-based offerings * How do you typically structure a first sales conversation with a business owner? * This role requires consistent follow-up. How do you personally manage follow-up so nothing slips through the cracks? * What do you do when a prospect says, "I need to think about it" or "Let me talk to my partner?" * How many hours per week are you realistically able to commit to a results-driven role? * Describe a time you missed a goal or quota. What happened, and what did you change afterward? * How comfortable are you discussing numbers like margins, cash flow, and profitability with business owners? * What does a "good week" in sales look like to you? * Why should we choose you over other candidates? Be specific. Work Location: Hybrid remote in Pittsburgh, PA 15236