VP, Sales Operations and Enablement (1576)
Fully Remote San Jose, CA Sales
Job Type

About CloudBees

CloudBees provides the leading software delivery platform for enterprises, enabling them to continuously innovate, compete, and win in a world powered by the digital experience. Designed for the world's largest organizations with the most complex requirements, CloudBees enables software development organizations to deliver scalable, compliant, governed, and secure software from the code a developer writes to the people who use it. The platform connects with other best-of-breed tools, improves the developer experience, and enables organizations to bring digital innovation to life continuously, adapt quickly, and unlock business outcomes that create market leaders and disruptors.

CloudBees was founded in 2010 and is backed by Goldman Sachs, Morgan Stanley, Bridgepoint Credit, HSBC, Golub Capital, Delta-v Capital, Matrix Partners, and Lightspeed Venture Partners. Visit www.cloudbees.com and follow us on Twitter, LinkedIn, and Facebook.

Key Responsibilities:

  • Act as Chief of Staff for the CRO, a proxy for the CRO to Sales and Sales Engineering, Channels, CS, PS, Operations, and Enablement
  • Act as Critical Issues/Escalation Manager for the CRO
  • Manage Territory and Quota assignment process, including categorization and sizing of accounts
  • Allocate headcount based on territory demand and market sizing data
  • Design and write the Variable Compensation Plan for quota-bearing sales reps, sales engineers, sales leadership, and sales development reps
  • Manage the Commission Appeal Process and act as the first line of adjudication for appeals
  • Partner with Finance and Legal to develop processes to streamline the back-office sales flow
  • Partner with Finance to analyze rep effectiveness
  • Partner with Product, Marketing, Finance, and Legal to create and administer Limited Availability Program for new product sets
  • Partner with key stakeholders to assist in the development of Go-To-Market strategies
  • Work with CRO to create Board and Executive-level presentations about the current and future state of the Sales and Client Services Organization
  • Partner with Enterprise Systems to scope and improve Sales-focused tools
  • Provide strategic sales and deal shaping support to sales on a deal basis
  • Partner with senior sales leadership to identify opportunities for sales process and methodology improvement
  • Design new sales coverage models, compensation plans, and incentive structures and operationalize them while balancing growth and ROI
  • Refine the sales management processes, including key performance indicators and dashboards, pipeline management, and account and territory planning
  • Lead, manage, and develop the Sales Operations team to deliver effective and accurate sales data and customized sales development programs
  • Proactively identify opportunities to improve the processes, communication, and management of sales performance to promote the scale and growth of the sales organization


  • Bachelor's degree required; advanced degree preferred
  • 10+ years of experience in a Leadership role for Sales Operations
  • 5+ years management experience
  • Experience in developing and administering Sales Compensation plans
  • Strong writing and analytical skills
  • Experience in some or all of the following areas: Sales operations; territory design and coverage models; sales process design; sales compensation planning; sales force automation (SFA) implementation and management; forecast/pipeline management; sales intelligence; data science, and data analysis
  • Customer-facing skills (strong presenter, comfortable with executive-level audience, able to identify issues/needs through effective questioning)

We’re invested in you!

We offer competitive benefits packages, opportunities for professional development, and more. We also offer generous paid time off to allow our employees time to rest, recharge and to be present with family and friends throughout the year.

At CloudBees, we truly believe that the more diverse we are, the better we serve our customers.  A global community like Jenkins demands a global focus from CloudBees. Organizations with greater diversity—gender, racial, ethnic, and global—are stronger partners to their customers.  Whether by creating more innovative products, or better understanding our worldwide customers, or establishing a stronger cross-section of cultural leadership skills, diversity strengthens all aspects of the CloudBees organization.

In the technology industry, diversity creates a competitive advantage.  CloudBees customers demand technologies from us that solve their software development, and therefore their business problems, so that they can better serve their own customers.  CloudBees attributes much of its success to its worldwide work force and commitment to global diversity, which opens our proprietary software to innovative ideas from anywhere. Along the way, we have witnessed firsthand how employees, partners, and customers with diverse perspectives and experiences contribute to creative problem-solving and better solutions for our customers and their businesses.