Director of Business Development
Paylocity
Description
The Director of Business Development is the senior, hands-on leader responsible for the day-to-day execution and performance of Pyramid Systems’ Growth organization. The Director develops and executes Pyramid’s federal growth strategy, leads the Growth team, drives new business, protects and expands existing business, and generates sustainable revenue growth across federal civilian and defense agencies.
This is a player-coach role requiring both leadership and direct execution. The Director is expected to personally build customer relationships, open doors, identify and qualify opportunities, gather market intelligence, lead capture, develop teaming strategies, support proposal development, and drive opportunities from identification through award while holding the Growth team accountable for results.
The Director owns Pyramid’s actionable federal pipeline and ensures opportunities are properly qualified, prioritized, resourced, pursued, and advanced. The Director works closely with executive leadership, Operations, Technical Leadership, Marketing, Recruiting, Contracts, and Proposal resources to convert Pyramid’s growth objectives into measurable bookings and revenue.
Three priorities are central to this role: protect and win Pyramid’s strategic recompetes, generate new federal services business, and accelerate the sale and adoption of AIR-Quire and Pyramid’s other AI-enabled solutions.
Requirements
Essential Job Functions
- Lead the day-to-day activities and performance of Pyramid’s Growth organization, establishing priorities, ownership, expectations, and measurable outcomes.
- Serve as a player-coach, personally performing business development and capture activities while leading, mentoring, and holding Growth team members accountable for execution and results.
- Develop and execute a federal growth strategy aligned with Pyramid’s corporate revenue, capability, market, and product objectives.
- Personally identify, qualify, develop, and pursue new opportunities across federal civilian and defense agencies.
- Build and maintain trusted relationships with federal executives, acquisition officials, program leaders, technology leaders, mission stakeholders, and industry partners.
- Leverage a current federal and industry network to generate customer meetings, market intelligence, qualified opportunities, strategic introductions, teaming relationships, and increased awareness of Pyramid.
- Own and actively manage Pyramid’s business development pipeline, ensuring it is accurate, qualified, actionable, appropriately prioritized, and supported by clear next steps and ownership.
- Ensure significant pursuits have sufficient customer and competitive intelligence, acquisition strategy, incumbent information, customer relationships, win strategy, teaming strategy, milestones, next actions, and realistic probability of win.
- Lead a disciplined Growth operating cadence covering pipeline health, customer engagement, capture progress, proposals, partnerships, recompetes, AIR-Quire sales, risks, actions, and upcoming decisions.
- Provide executive leadership with accurate and candid reporting regarding pipeline health, opportunity status, probability of win, expected bookings, investments, resource requirements, and risks.
- Make disciplined pursue/no‑pursue and bid/no‑bid recommendations based on strategic fit, customer access, competitive position, probability of win, resources, revenue potential, and return on investment.
- Lead opportunity shaping and capture, including customer engagement, competitive assessments, acquisition strategy, teaming, solution positioning, win themes, pricing considerations, and capture planning.
- Drive opportunities from identification and early shaping through solicitation, proposal, evaluation, award, and transition to Operations.
Recompetes and Protecting the Base
- Lead the Growth strategy and execution required to protect and retain Pyramid’s strategic incumbent business and win critical recompetes.
- Begin recompete positioning well in advance of solicitation release, incorporating customer engagement, performance assessments, competitive intelligence, acquisition strategy, teaming, solution improvements, pricing considerations, win themes, discriminators, and capture planning.
- Establish clear ownership, milestones, and executive visibility for strategic recompetes and ensure Growth, Operations, Technical, Contracts, and Proposal resources are aligned around the win strategy.
- Proposal Quality and Accountability
- Own the overall business quality and competitiveness of Pyramid’s RFP, RFQ, RFI, Sources Sought, white paper, and other strategic responses.
- Serve as the senior Growth leader responsible for the final business and capture review of major submissions before executive approval, ensuring each response is complete, compelling, responsive, professionally presented, differentiated, and positioned to win.
- Partner with Proposal/Compliance, Contracts, Technical Leadership, Operations, and subject matter experts to ensure solicitation requirements are fully addressed and submissions are compliant, accurate, consistent, and delivered on time.
- Ensure proposal development begins with a clear capture strategy, customer intelligence, competitive assessment, win themes, discriminators, solution approach, teaming strategy, and pricing strategy rather than waiting until an RFP is released to develop the pursuit strategy.
- Personally review and challenge proposal content for quality, responsiveness, clarity, differentiation and persuasiveness and direct corrective action when gaps exist.
- Establish and enforce appropriate proposal review milestones and quality‑control processes, including color‑team or equivalent reviews, allowing sufficient time for meaningful technical and executive review.
- Hold the Growth team accountable for producing high‑quality, compliant, competitive proposals designed to win—not simply proposals that meet submission deadlines.
AIR-Quire and Product Growth
- Make the successful commercialization of AIR-Quire a priority Growth objective and personally lead the strategy for expanding its adoption across the federal market.
- Develop a qualified AIR-Quire pipeline with identified agencies, customer champions, decision‑makers, acquisition strategies, funding paths, contract vehicles, partners, next actions, and anticipated award timelines.
- Drive customer demonstrations, sandbox evaluations, follow‑up activities, acquisition discussions, partnerships, and contract vehicle strategies designed to convert customer interest into funded opportunities.
- Achieve a minimum annual objective of two new AIR-Quire sales/contract awards, unless otherwise adjusted by executive leadership through Pyramid’s annual Growth plan.
- Support the market development and commercialization of future Pyramid AIR products and other AI-enabled solutions.
- Partnerships, Market Presence and Team Execution
- Identify, establish, negotiate, and manage strategic relationships with prime contractors, subcontractors, technology companies, contract vehicle holders, and other industry partners.
- Work collaboratively with Marketing to strengthen Pyramid’s federal market presence, brand awareness, thought leadership, campaigns, events, and targeted customer outreach.
- Represent Pyramid professionally at customer meetings, industry events, conferences, networking forums, partner meetings, demonstrations, and other business development activities.
- Contribute directly to capture plans, white papers, proposals, presentations, demonstrations, customer briefings, and other Growth deliverables as required.
- Ensure Growth deliverables represent complete, high‑quality staff work and that customer, partner, and executive commitments are tracked and completed on time.
- Establish measurable individual and team expectations and hold Growth personnel accountable for customer engagement, opportunity development, capture milestones, proposal support, bookings, revenue, and results.
Knowledge/Skills/Abilities
- Proven federal business development leader with a demonstrated record of generating measurable revenue growth and winning federal business.
- Strong player‑coach mentality with the willingness and ability to lead the Growth organization while personally executing business development, customer engagement, capture, partnering, and proposal activities.
- Demonstrated ability to lead, develop, motivate, and hold a Growth team accountable for measurable results.
- Highly organized and detail‑oriented with strong pipeline, opportunity, capture, proposal, and action‑management discipline.
- Proactive self‑starter who independently identifies opportunities, develops relationships, solves problems, and drives pursuits forward without requiring extensive direction or follow‑up.
- Strong understanding of the difference between a large pipeline and a qualified, actionable pipeline with a realistic path to award.
- Current and demonstrable federal and industry relationships with the ability to independently generate customer access, business intelligence, teaming opportunities, and qualified pursuits.
- Strong capture‑management skills, including customer engagement, competitive analysis, teaming, solution development, win strategy, pricing considerations, and proposal positioning.
- Strong understanding of federal proposal development, compliance, review processes, and the elements required to produce compelling and competitive responses.
- Strategic thinker capable of translating corporate growth objectives into executable plans, assignments, milestones, and measurable results.
- Strong executive presence and exceptional written, verbal, presentation, relationship‑development, and negotiation skills.
- Strong business judgment, including the willingness to stop pursuits when customer intelligence, competitive positioning, resources, or probability of win no longer justify continued investment.
- Data‑driven decision maker with strong forecasting, reporting, pipeline analytics, and performance‑management capabilities.
- Strong sense of ownership, urgency, personal accountability, and follow‑through.
- Ability to operate successfully in a small to mid‑sized federal contractor where leaders are expected to be flexible, resourceful, collaborative, responsive, and directly involved in execution.
- Understanding of AI‑enabled solutions and experience positioning technology, digital transformation, software, or AI solutions within the federal marketplace is highly desirable.
Qualifications
- Bachelor’s degree required; advanced degree or relevant business development/capture certifications preferred.
- Minimum of 10 years of progressive federal business development, capture management, account management, sales, or Growth leadership experience.
- Demonstrated record of personally contributing to and leading significant federal contract wins and generating measurable new‑business revenue.
- Proven experience building, qualifying, managing, and converting federal pipelines into contract awards.
- Demonstrated experience leading business development, capture, account, proposal, or other Growth professionals.
- Experience successfully pursuing federal opportunities ranging from approximately $10M to $100M+ in total contract value.
- Current and relevant relationships across federal civilian and/or defense agencies and the federal contracting community.
- Thorough understanding of the federal procurement lifecycle, FAR-based acquisitions, GWACs, IDIQs, BPAs, task‑order competitions, GSA Multiple Award Schedule opportunities, and other federal acquisition vehicles.
- Experience leading capture from early identification and shaping through solicitation, proposal, evaluation, and award.
- Experience developing teaming strategies and negotiating relationships with large and small federal contractors and technology partners.
- Demonstrated ability to operate effectively in a small to mid‑sized government contracting environment where initiative, urgency, adaptability, accountability, and hands‑on execution are essential.
- Experience with federal business intelligence and market research tools such as GovWin, SAM.gov, Bloomberg Government, FPDS, and successor federal procurement data systems.
Measures of Success
- Success in this role will be measured by results, not activity alone, including:
- Achievement of a minimum of two new AIR-Quire sales/contract awards annually.
- Successful retention and recompete wins of Pyramid’s strategic incumbent contracts.
- New federal services contract awards, bookings, and sustainable revenue growth.
- Growth, quality, advancement, and conversion of the qualified pipeline.
- Early positioning and capture readiness for strategic recompetes and priority pursuits.
- Quality, compliance, competitiveness, and win rate of proposal submissions.
- Development of new federal customer relationships and expansion of existing accounts.
- Conversion of customer meetings, demonstrations, and evaluations into qualified and funded opportunities.
- Development of productive strategic partnerships and teaming relationships.
- Accuracy and reliability of pipeline reporting and forecasting.
- Effectiveness, accountability, and performance of the Growth team.
- Achievement of Pyramid’s annual Growth, bookings, and revenue objectives.
The Director of Business Development is expected to take ownership of Pyramid’s Growth mission: protect the base, win new business, grow AIR-Quire, lead the team, and deliver results.
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