Ultimate Software

VP. Sales

Ultimate Software • $140K — $210K *
US-AnywhereRemote in United States
Enterprise Technology
11 - 15 years of experience
Job Overview by Ladders

Qualifications

  • 12+ years in B2B tech, SaaS, or complex solution sales.
  • 7+ years leading sales teams; minimum 3 years at multiple management levels.
  • Experience owning a significant revenue-targeted sales organization in a defined geography.
  • Leading an organization of over 20 employees through multiple management layers.
  • History of developing and executing long-term aligned sales strategies.

Responsibilities

  • Develop and implement regional sales strategy aligned with company objectives.
  • Lead multi-layer sales teams across the region.
  • Set clear performance expectations for sales metrics and execution.
  • Translate business strategies into effective regional plans.
  • Conduct regular reviews for forecasts and team performance.
  • Coach directors and managers to enhance their team's effectiveness.
  • Identify performance risks using market and customer data.

Benefits

  • Opportunity to participate in a performance-based incentive compensation plan.
  • Eligibility for commissions and restricted stock units as part of total compensation.
  • Access to professional development and career progression opportunities.
Full Job Description
About the Role

The Vice President, SMB Sales East is responsible for leading the sales strategy, execution, and performance of an assigned geographic segment within UKG's expanded SMB organization, serving customers with approximately 1-500 employees.
Reporting to the leader of SMB Sales, this role oversees multiple sales teams and layers of leadership across the assigned region. The VP will translate the broader SMB strategy into a focused regional operating plan, drive predictable revenue performance, develop sales leaders, and ensure the organization delivers strong customer and business outcomes.
This leader serves as the senior sales executive for the assigned geography and partners closely with Sales Operations, Marketing, Finance, Solutions Consulting, Customer Success, and other cross-functional teams to optimize coverage, productivity, talent, and growth.
Key Responsibilities
• Develop and execute the sales strategy for the assigned geographic SMB segment in alignment with UKG's broader business objectives.
• Lead a multi-layer organization of sales leaders and teams across the assigned region.
• Establish clear expectations for bookings, pipeline generation, productivity, forecast accuracy, customer engagement, and sales execution.
• Translate market opportunity and business strategy into effective territory, capacity, and resource plans.
• Drive consistent operating rhythms, including business reviews, forecast calls, pipeline reviews, talent discussions, and performance inspections.
• Coach and develop directors, senior managers, and frontline sales leaders to improve team performance and leadership effectiveness.
• Build a strong leadership pipeline through hiring, succession planning, talent development, and internal mobility.
• Monitor regional performance and use business, customer, and market data to identify risks, make informed decisions, and adjust priorities.
• Partner with Finance and Sales Compensation to ensure quotas, compensation programs, and investments appropriately support regional performance and organizational health.
• Collaborate with Marketing, Sales Operations, Solutions Consulting, Customer Success, and other functions to improve seller productivity and customer outcomes.
• Build trusted relationships with strategic customers and partners within the assigned geography.
• Promote a culture of accountability, collaboration, inclusion, customer focus, and continuous improvement.
• Lead organizational change with clarity, transparency, and urgency.
• Represent the geographic segment in SMB planning, executive reviews, and enterprise decision-making.
• Ensure short-term execution is balanced with long-term organizational capability and sustainable growth.

Required Qualifications
• 12+ years of progressive experience in B2B technology, SaaS, or complex solution sales.
• 7+ years of experience leading sales teams, including at least 3 years leading through multiple levels of management.
• At least 3 years of experience owning a geographic, regional, or market-based sales organization with responsibility for multiple teams and a significant revenue target.
• Demonstrated experience leading an organization of more than 20 employees, preferably through directors, senior managers, and frontline managers.
• Demonstrated success developing and executing long-term sales strategies aligned with broader company objectives.
• Proven record of delivering revenue growth, bookings, pipeline health, productivity, and forecast accuracy.
• Experience managing regional workforce planning, staffing, budgeting, expense priorities, territory design, capacity planning, and resource allocation.
• Experience partnering with Finance, Sales Compensation, Sales Operations, Marketing, Customer Success, Solutions Consulting, and other cross-functional leaders.
• Demonstrated ability to navigate complex and ambiguous business situations, assess risk, and make effective course corrections.
• Experience leading through organizational change, growth, integration, or transformation.
• Demonstrated success hiring, coaching, developing, and succession-planning sales leaders.
• Strong commercial, financial, analytical, and operational business acumen.
• Executive presence, sound judgment, courage, and the ability to influence senior stakeholders.
• Bachelor's degree or equivalent experience.
Preferred Qualifications
• Prior experience in a Vice President, Regional Vice President, General Manager, or comparable senior sales leadership role.
• Experience leading SMB, emerging, commercial, or mid-market sales organizations.
• Experience managing a geography with a mix of customer segments, sales motions, or channels.
• Experience in a global or matrixed organization.
• Experience with workforce management, HR technology, payroll, or related SaaS solutions.

The base salary range for this position is $140K - $210K annually, with the opportunity to significantly increase total earnings through a performance-based incentive compensation plan. The plan may provide for the payment of commissions and restricted stock unit awards as part of total compensation. The base pay offered may vary depending on skills, experience, job-related knowledge, and work location. Learn more about UKG's benefits and rewards at https://www.ukg.com/about-us/careers/benefits

About Ultimate Software

Ultimate Software is a leading provider of cloud-based human capital management (HCM) solutions. The company's UltiPro platform offers a comprehensive suite of HR, payroll, and talent management tools designed to help organizations manage their workforce more effectively. Ultimate Software was founded in 1990 and is headquartered in Weston, Florida. The company has received numerous awards for its workplace culture and has been recognized as one of the best places to work in the United States. In 2019, Ultimate Software was acquired by private equity firm Hellman & Friedman in a deal valued at $11 billion.
Learn more about Ultimate Software
Size
5,600 employees
Industry
Founded
1990

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