Senior Director, GTM Strategy and Operations

Senior Director, GTM Strategy and Operations
Customer Success I San Francisco, CA or Seattle, WA or Chicago, IL

This position is not eligible for employment in the following states: Alaska, Hawaii, Maine, Mississippi, North Dakota, South Dakota, Vermont, West Virginia and Wyoming.

Our agreement with employees
DocuSign is committed to building trust and making the world more agree-able for our employees, customers and the communities in which we live and work. You can count on us to listen, be honest, and try our best to do what’s right, every day. At DocuSign, everything is equal. We each have a responsibility to ensure every team member has an equal opportunity to succeed, to be heard, to exchange ideas openly, to build lasting relationships, and to do the work of their life. Best of all, you will be able to feel deep pride in the work you do, because your contribution helps us make the world better. And for that, you’ll be loved by us, our customers, and the world in which we live. 

The team
Our Customer Success team is the largest organization in the world focused entirely on agreement processes and technologies. We are the Agreement Experts. With hundreds of thousands of successful customers worldwide, we know how to help our customers see results quickly. And that experience is just one of the reasons our customers trust us to connect, automate, and integrate their systems of agreement, everywhere they need to get work done. As part of our global team of Agreement Experts – in professional services, customer success management, learning and enablement, and customer support – you’ll bring your knowledge, insights, and proven expertise to help our customers achieve more than they ever thought possible.

The position 
The Senior Director is a key role in the Customer Success Strategy and Operations organization. The Senior Director is focused on ensuring there is a seamless Customer Success GTM strategy through the pre and post sales motions with a customer-first point of view. This leader will be responsible for incorporating and streamlining Customer Success touchpoints into the overall DocuSign GTM strategy during the sales cycle. This leader will also collaborate with the post-sales cross-functional team within DocuSign and our partner ecosystem to ensure Customers have positive experiences throughout their customer journey. 

This role is responsible for defining and driving the Services GTM strategy for each DocuSign customer segment, from small businesses to large multinational enterprises. The Sr. Director, Global Success GTM Strategy will support the achievement of Services bookings and revenue  targets by developing, refining, and optimizing the Services GTM Strategy and driving towards an increased attack of services supporting adoption, retention, and upsell.

The Senior Director will be working closely with the Pricing and Packaging, Marketing, and Enablement teams to develop service playbooks and GTM strategies that are packaged, deployed and enabled across Sales and Customer Success globally. This role also ensures that these motions and services are scaled to resonate within each market segment appropriately. This role will perform ongoing analysis to measure the effectiveness of GTM strategies and programs and continuously improve with ongoing business changes. 

The Senior Director, GTM Strategy and Operations is a senior strategic role responsible for leading day-to-day operations for the Americas Professional Services business. The role will own Business Process Management, Resource and Capacity Management, and Revenue Management functions, as well as key cross-functional partnerships with Sales, Customer Success, Technical Best-in-class Support, and GTM Strategy teams. By maintaining an impactful, efficiently functioning operational engine, this leader will ensure our Services business delivers on customer commitments as well as on our business metrics. You will lead directly and by influence to ensure our global Services business is adopting standard methodologies and completing global priorities!

A successful candidate will need to partner strongly across global and regional teams, understand all of DocuSign’s products and how Services should be applied to deployments, have high acumen for learning new technologies and business drivers, and be skilled in developing services plays and GTM strategies that incorporate into DocuSign’s overall GTM strategy.

This position is a people manager reporting to the VP of Global Customer Success Operations & Strategy and is designated Flex.


  • Develop CS GTM vision and drive a strategy across the customer journey (pre and post sales)
  • Design a CS GTM strategy based on internal and external research, market analysis, and customer segmentation
  • Evangelize GTM strategy by engaging cross-functional teams in a matrixed organization including Sales, Marketing, Partner Success, Customer Success, Operations and Product
  • Establish strong partnerships and interlock with GTM, Sales, Partners and Customer Success to optimize product services attach rates in all segments
  • Embed Success into the DocuSign GTM strategy
  • Align closely with these teams to understand GTM needs and develop plays, offerings, packages, accelerators, and programs that support Customer outcomes, experiences, and realization of product value
  • Define and coordinate business process standard and best in class practices that enable our Service Sales and Delivery teams to efficiently engage with customers and partner effectively with other teams at DocuSign
  • Design and lead a robust framework for Project Health and Customer Satisfaction including reporting, inspection, and action
  • Drive leadership around business requirements for the design and rearchitecting of our Financial Force system
  • Lead the Resource Management Office, ensuring effective resource management operations focusing on strategy and execution
  • Own the capacity planning process based on the annual planning cycle
  • Evaluate and analyze effectiveness of Services portfolio and GTM programs
  • Measure KPIs and establish a strong financial and operational foundation and cadence for measuring the business
  • Use data to drive decisions and insights that inform and direct the business
  • Build out a monthly and quarterly close packet that drives business insights to make appropriate changes in the business
  • Drive alignment across regions and shared functions to drive and execute GTM in a globally consistent way, while taking into account regionally specific needs
  • Gain alignment within a large cross-functional organization to deploy new strategies and motions that positively impact DocuSign’s business
  • Manage a team of 10-15 resources across multiple areas of the business

Basic qualifications

  • BS/BA degree in Business Management, Operations, Accounting, or Finance  
  • 15+ years of experience working at a SaaS company
  • 15+ years of experience in Customer Success and/or Management Consulting 
  • 10+ years leading operational teams within a Professional Service Organization 

Preferred qualifications

  • MBA in Business Management, Operations, Accounting or Finance
  • Expert knowledge of SaaS business and Customer Success and Professional Services measure
  • Technical acumen to learn new technologies, map systems and processes, and provide consultative guidance
  • Skilled in business transformation
  • Experience with P&L management
  • Strong experience and understanding of SI and ISV partner relationships
  • An ability to drive change with a customer experience focused mindset
  • Successful experience working with matrixed global organizations
  • Superior skills at relationship-building, cross-organizational partnering, and driving results through influence and negotiation
  • Excellent communication and presentation skills, both verbal and written

Vaccination requirement 
DocuSign may require all employees to be fully vaccinated against COVID-19 and provide proof of vaccination to visit a DocuSign office, to meet with potential or actual customers or business partners, or for other business-related purposes, in accordance with local law. Please note that DocuSign has contracts with different governments globally which may require compliance with local and federal laws.

About us
DocuSign helps organizations connect and automate how they prepare, sign, act on and manage agreements. As part of the DocuSign Agreement Cloud, DocuSign offers eSignature, the world's #1 way to sign electronically on practically any device, from almost anywhere, at any time. Today, over a million customers and more than a billion users in over 180 countries use the DocuSign Agreement Cloud to accelerate the process of doing business and simplify people's lives. And we help save the world’s forests and embrace environmental sustainability.

It's important to us that we build a talented team that is as diverse as our customers and where all employees feel a deep sense of belonging and thrive. We encourage great talent who bring a range of perspectives to apply for our open positions. DocuSign is an Equal Opportunity Employer and makes hiring decisions based on experience, skill, aptitude and a can-do approach. We will not discriminate based on race, ethnicity, color, age, sex, religion, national origin, ancestry, pregnancy, sexual orientation, gender identity, gender expression, genetic information, physical or mental disability, registered domestic partner status, caregiver status, marital status, veteran or military status, or any other legally protected category.

DocuSign provides reasonable accommodations for qualified individuals with disabilities in job application procedures, including if you have any difficulty using our online system. If you need such an accommodation, you may contact us at