Chief Strategy Officer



Charlottesville, VA, USA · Columbus, OH, USA · Durham, NC, USA
Posted on Thursday, May 11, 2023

Chief Strategy Officer

This role will maintain an in-office presence in a hybrid capacity from our Charlottesville, VA, office.

Who We Are

WillowTree, a TELUS International Company, partners with the world’s leading brands to help them tackle their thorniest challenges - be it launching new digital products, delivering personalized marketing at scale, or harnessing the power of data and AI to transform their business. These mission-critical initiatives aren’t solved by a single discipline. Great digital is a team game - it requires seamlessly combining strategy, engineering, design, data science, marketing, and more. Other firms have bolted on these capabilities - as digital natives, we’ve built them into our teams from Day 1. The result? Top and bottom lines that grow, alongside our client’s capabilities. Check out how we have impacted our clients' digital portfolios over the years.

In January 2023, WillowTree was acquired by TELUS International (Symbol: TIXT). The combined company brings an unparalleled ability to deliver seamless, trusted, digitally-enabled experiences across any channel a customer might choose - be it mobile apps, websites, voice skills, chatbots, email, service agents, or associates.

The Opportunity

WillowTree's Chief Strategy Officer will build the next phase of our strategy and advisory practice. Across an ever-growing portfolio of Fortune 500 clients we have the opportunity to play a stronger Trusted Advisor role as business strategy and digital strategy merge to become synonymous.

We are in the unique position to help clients truly assess technologies and their value within the enterprise, make investment decisions, architecture and vendor selection, develop and launch products and then manage/maintain those products and digital marketing efforts. Combined with TELUS International, we can offer clients additional critical digital capabilities including content moderation, AI annotation and digital customer experience/service. Supported by a global team of 1,200+ researchers, designers, engineers, data scientists, and marketers, we make strategy real. As we like to say, "Don't trust ideas from people who don't know how to build them."

Along the way, you’ll work closely with our firm’s C-Suite to articulate, and deliver, what it takes for WillowTree to win in an ever-competitive digital landscape.

The strategy team that this position will lead currently consists of world-class product strategists in place, driving human-centered innovation with many of our largest clients. Recent projects include:

  • Setting the digital portfolio strategy for a 130+ year old publishing leader
  • Reimagining the business model for a global fitness company
  • Creating an engaging, award-winning Super Bowl Halftime Show app, starting from a blank sheet of paper

Opportunities to enhance the existing practice include enhancing our corporate strategy capabilities, integrating new/broader WillowTree and TELUS International capabilities into our recommendations (e.g., AI/ML), ensuring equal emphasis on business viability and financial modeling, and expanding the conversations where WillowTree credibly serves as a Trusted Advisor.

As the leader of the evolved Strategy practice, you’ll balance your time between select client engagement points and team leadership, business development, and talent acquisition.

What’s in it for the right candidate?

  • An opportunity to build a world class strategy practice from the ground up
  • Internal support from some of the best engineering and design teams in the world
  • Opportunity to see their work create real, tangible value out in the world, beyond just a glossy presentation (i.e., a new product coming to market; clients flexing new capabilities)
  • Travel on an as-needed basis, rather than the Monday through Thursday schedule more typical of traditional strategy consulting
  • Dedicated time for thought leadership
  • Chance to flex commercial acumen via pitches and proposals, but with the support of a robust, dedicated commercial enablement team (i.e., we don’t do pitch work in our ‘spare time’)
  • Collegial, team-first environment - working amongst a wide variety of disciplines and more than a few former consultants (e.g., Monitor Group; AT Kearney; Deloitte)
  • Access to over 650+ of the world's most admired brands who are currently clients of TELUS International and WillowTree


  • Manage, lead, and evolve the WillowTree Strategy practice - a critical strategic initiative for the firm, reporting to the CEO
  • Build the practice and the team — bring perspective on structure and shape of the team as we invest in and continue to grow it
  • Identify new areas and client challenges for WillowTree’s strategic advisory services, and methodical approaches to tackling them
  • Tell compelling and inspiring stories through artfully crafted presentations outlining the research, vision, and specific recommendations balanced with business viability and technical feasibility
  • Partner with business development to develop proposals, provide estimations, and prepare pitches
  • Serve as point of contact and escalation for key client stakeholders
  • Evolve the direction of the WillowTree Consulting group, in collaboration with product and marketing leaders across the firm
  • Evolve the WillowTree strategy framework, and develop training modules for the strategy team and others across the business (leveraging outside experts as necessary)
  • Partner with our Marketing department to develop thought leadership on behalf of WillowTree and drive inbound inquiries into the firm


  • Extensive consulting experience at a premium management consulting firm leading digital strategy and digital transformation projects for F500 organizations
  • Project experience in product and portfolio management, roadmap prioritization, ROI analysis / financial modeling, org design, M&A due diligence, scenario planning, go-to-market strategy and positioning
  • Conversant in best practices in loyalty, conversion, segmentation, engagement and retention and the ability to translate to a digital context
  • Experience marrying design thinking with business strategy and emerging technologies -- including a deep love of tech and everything it can do
  • 8+ years of prior management experience, embodying a ‘servant leadership’ mindset and approach, managing a team of strategists and consultants
  • Strong storyteller— can direct and lead presentations with senior (C-level) audiences across stakeholders - the CEO, CTO, CMO and CFO
  • Familiarity with the latest advances in marketing technology
  • Deep sense of creativity — oftentimes our clients are looking for inspiration and direction — genuine enthusiasm/creativity in coming up with solutions for brands/clients
  • MBA, undergrad or similar business degree
  • Significant technical background either via a degree or extended exposure

Why WillowTree?

We offer a place to be yourself.

Our differences, both visible and invisible, benefit our teams, our communities, and the products we craft. That’s why WillowTree strives to build a team with diverse backgrounds, skills, and perspectives. You’ll work hard here; however, we’ll balance that with a culture that supports your growth and cares about your well-being. We’re committed to creating an environment of inclusion — a place where every Tree can thrive.

We want you to reach your fullest potential and part of your professional development at WillowTree will include dedicated time to innovate on passion projects and an annual stipend to fund your professional pursuits.

WillowTree upholds our core values in every aspect of our work. We promote safe and inclusive work environments and maintain a drug-free workplace. We celebrate our differences and provide equal employment opportunities to all team members and applicants without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. Diverse teams build better products. We acknowledge that the tech industry especially lacks opportunity for those who are of non-traditional backgrounds and in underrepresented groups. In order to create the best products for everyone, we know that it's important for our team to reflect the diversity of our users, and we are committed to being the change we want to see.