Offering Lead (Data and AI)

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Thoughtworks is seeking an Offering Lead for Data and AI to own a data modernization portfolio in North America, leading opportunities, guiding delivery, and ensuring measurable business outcomes for clients. The role blends market sensing, pipeline strategy, executive client and partner engagement, and CXPD leadership to co-shape strategy, establish enablement, and capture reusable assets. Ideal candidates bring consultative sales, solution shaping, and complex pursuit experience, with a proven ability to influence VP/C-suite stakeholders in a matrix and tell compelling stories that win deals. To apply, tailor your resume to show roadmaps, high-stakes RFPs, cross-functional leadership, and partner collaboration. Onsite in Toronto, full-time, CAD 159k-309k, benefits link, AI policy link.

The Data and AI Offering Lead is an expert on Data Modernization focused on building and growing a portfolio of work across North America.

They act as a “leader among leaders” on Data and AI pursuits and engagements, shaping opportunities, influencing delivery, and ensuring the offering delivers measurable business outcomes for clients and for Thoughtworks.

Job responsibilities

• Market & offering
  • Sensing demand across key accounts and markets.
  • Sharpening positioning, narratives, and “plays” for the offering.
  • Partnering with Marketing and global Data and AI to evolve assets, demos, and stories.
• Pipeline & pursuits
  • Qualifying opportunities for SPARK involvement.
  • Assigning Offering Architects/strategists and setting pursuit strategy.
  • Leading solution/value shaping and proposal storyline.
  • Coordinating with sales, Deal Desk, and SPARK leadership on major deals.
• Client & partner engagement
  • Building executive relationships in priority accounts.
  • Leading high‑stakes conversations that connect modernization/platform journeys to business outcomes.
  • Working with partners (e.g., hyperscalers, modernization partners) where they are integral to the offering’s story.
• Internal leadership
  • Co‑shaping CXPD strategy and operating model.
  • Running enablement and communication rhythms for the offering 
  • Ensuring knowledge, case studies, and SOW patterns are captured and reused.

Job qualifications

Technical Skills

• You have a passion and perseverance for creating best in class software products that deliver outstanding customer experiences and business outcomes.
• Extensive experience in consultative sales, solution shaping, and/or account leadership within Product Development and Technology.
• Seasoned Data Modernization thinker with the ability to shape an engagement, translate into a roadmap with clear business and customer outcomes.
• Proven track record of leading complex pursuits and working as a peer with senior client stakeholders (VP/C‑suite) and internal leadership in a matrix environment.

Professional Skills

• Demonstrated ability to influence without formal authority, orchestrate diverse teams (sales, delivery, partners), and maintain clarity under ambiguity.
• Excellent storytelling, facilitation, and negotiation skills, with comfort operating in high‑stakes, time‑boxed situations (RFPs, QBRs, executive workshops).

Other things to know

Learning & Development

There is no one-size-fits-all career path at Thoughtworks: however you want to develop your career is entirely up to you. But we also balance autonomy with the strength of our cultivation culture. This means your career is supported by interactive tools, numerous development programs and teammates who want to help you grow. We see value in helping each other be our best and that extends to empowering our employees in their career journeys.

About Thoughtworks

Thoughtworks is a dynamic and inclusive community of bright and supportive colleagues who are revolutionizing tech. As a leading technology consultancy, we’re pushing boundaries through our purposeful and impactful work. For 30+ years, we’ve delivered extraordinary impact together with our clients by helping them solve complex business problems with technology as the differentiator. Bring your brilliant expertise and commitment for continuous learning to Thoughtworks. Together, let’s be extraordinary.

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Salary

Benefits: https://www.thoughtworks.com/en-ca/careers/benefits

See here our AI policy.