Senior Director, Commercial Finance Deal Desk

Set the vision, priorities, and multi-year roadmap for Commercial Finance Deal Desk, aligning its governance model and resources with UKG's growth plans, financial objectives, and evolving enterprise deal landscape. Lead, develop, and retain a high-performing team; set clear expectations, build financial and commercial judgments, and create a consistent service model for senior stakeholders and deal teams. Serve as a trusted advisor to the CRO, CFO, and other executive leaders on material deal decisions, presenting concise analysis, recommendations, risks, and alternatives to support timely decisions. Partner with Sales leadership and cross-functional teams to develop scalable financial tools and guidance for the seller toolkit, helping sellers assess deal options, structure strategic transactions, and move opportunities forward within UKG's financial and policy guardrails. Identify opportunities for targeted sales plays and lead the financial strategy, deal frameworks, and enablement needed to help teams pursue them consistently and effectively. Direct the financial assessment of complex deal structures, including implications for margin, revenue, cash flow, financial commitments, risk, and other relevant business outcomes. Own and continually improve the deal review and approval framework, including policy interpretation, approval authorities, decision rights, exception criteria, and escalation paths. Enforce company policies and approved pricing decisions, identify material deviations, and ensure exceptions receive appropriate review and documented approval. Partner with Sales, Legal, FP&A, Accounting, Product, Sales Operations, and other senior stakeholders to evaluate deal options and develop commercially workable structures within UKG's financial and policy guardrails. Use portfolio-level data and deal trends to identify recurring exceptions, margin patterns, policy gaps, and process risks; translate findings into recommendations for executive leaders and changes to governance or commercial practice. Lead finance workstreams for strategic commercial initiatives, including Salesforce CPQ design and implementation, deal workflow and reporting improvements, and related quote-to-cash transformation efforts. Establish performance measures for the function, including deal mix, exception trends, review quality, cycle times, and financial outcomes; use them to improve capacity, consistency, and business impact. Develop and deliver targeted guidance and enablement so stakeholders understand financial requirements, policy expectations, and the information needed to make sound deal decisions. You are an experienced finance leader who can shape strategy, lead a team, and influence decisions at the executive level. You are effective at turning transaction-level analysis into broader insight, setting clear direction for a function, and building partnerships that improve how the organization makes and executes decisions. What You Bring Significant leadership experience in commercial finance, deal desk, strategic finance, corporate finance, or a related function in a SaaS or technology business. Demonstrated success leading and developing teams, setting functional direction, and building scalable operating processes. Strong understanding of enterprise SaaS economics and the financial considerations in complex transactions, including recurring revenue, margin, deal structure, payment terms, discounts, implementation or development fees, cash flow, and risk. Experience advising senior executives and presenting clear, well-supported recommendations on material financial or commercial decisions. Ability to establish and apply policies, approval frameworks, decision rights, and controls while maintaining effective business partnerships. Excellent analytical, communication, negotiation, and executive presentation skills, with the ability to explain complex issues clearly and directly. Experience with Salesforce CPQ or other quote-to-cash systems and large enterprise SaaS transactions. Experience building deal governance, exception reporting, financial approval workflows, or commercial enablement programs. Bachelor's degree in Finance, Accounting, Economics, or a related field Bachelor Degree 12 years of experience in commercial finance, deal desk, strategic finance, or corporate finance.