Senior Director, Commercial Finance Deal Desk

UKG•Lowell, MA

1d•$169,400 - $241,400

About The Position

The Commercial Finance Deal Desk is a function within the CAO organization, responsible for the financial governance of UKG’s largest and most strategic SaaS transactions. The team partners across Finance and with Sales, Legal, FP&A, Product, and other leaders to assess commercial proposals, apply company policy, and help UKG make disciplined, well-informed deal decisions. Reporting to the Vice President, Revenue, the Senior Director will set the strategy and lead the team responsible for finance review of material deal exceptions and nonstandard commercial terms. This leader will advise senior executives on the financial implications of proposed arrangements, establish consistent decision frameworks, and ensure that deal structures support UKG’s financial objectives while meeting policy and approval requirements. The role will build a scalable operating model for deal governance, clarifying decision rights, strengthening review and escalation paths that should inform policy and commercial practice. The Senior Director will also lead finance workstreams for strategic initiatives, including CPQ automated workflows, process transformation, and stakeholder enablement. The function provides financial leadership and governance.

Requirements

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.
Bachelor Degree
12 years of experience in commercial finance, deal desk, strategic finance, or corporate finance.

Nice To Haves

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

Responsibilities

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.