Senior Strategist, Enterprise

Brainstation; Toronto; Hybrid; CAD 121,000 - 142,000; Full time

Benefits offered by this job

Retirement Planning

Parental Leave Program

Flexible Working Hours

Work from Home Flexibility

Service Recognition Programs

Socials, Outings & Retreats

Culture of Learning & Development

Job summary

BrainStation is seeking a Senior Strategist, Enterprise to partner with global clients as they transform for the AI era. You will lead discovery, shape roadmaps, and present actionable AI and digital-opportunity insights to C-suite executives across functions.

You will guide strategic conversations, run executive workshops, and own proposals and engagement materials. The role emphasizes in-person collaboration in a hybrid model and frequent client travel.

Qualifications

• Bachelor’s degree or equivalent professional experience.
• 3–6 years in a client-facing role with enterprise clients.
• Ability to structure complex, ambiguous business problems.
• Strong executive presence and communication skills.
• Experience leading client workshops and discovery sessions.
• Interest in AI and digital technology and transformation.
• Willingness to travel globally for client work.

Responsibilities

• Build and deepen relationships with C‑suite executives and AI, Product, Marketing, Design, and Data leaders.
• Act as trusted advisor, guiding opportunity discovery and managing client engagements.
• Develop understanding of client business models and digital operating contexts.
• Lead discovery, current-state assessments, and synthesize findings.
• Design target-state capabilities and transformation roadmaps.
• Present advisory viewpoints on digital and AI innovations.
• Design and facilitate executive workshops and working sessions.
• Prepare proposals, presentations, and business cases for senior clients.
• Contribute to BrainStation’s AI and innovation thought leadership.

Skills

Client-facing

Executive communication

Strategic thinking

Executive workshop leadership

Travel readiness

Cross-functional collaboration

Education

Bachelor’s degree or equivalent professional experience

Job description

As a Senior Strategist, Enterprise, you will work with global organizations as they transform for the AI era. Our clients are leaders in their industries, operating across markets worldwide, and we work with their C‑suites and business leaders as well as the executives who run their AI, Product, Marketing, Design, and Data teams. The role operates on two fronts. First, you will help these enterprises build durable, organization‑wide AI capability: the skills, processes, tools, and digital operating models their people need to work differently. On the second, you will advise senior leaders on the digital and AI innovation opportunities emerging in their industries, including how AI will reshape the products they build and the customer experiences they deliver.

This is transformation work, and at this level you will own significant parts of it. You will lead discovery, form the point of view on where a client stands and where they need to be, and shape the roadmap that gets them there. You follow developments in AI and digital technology closely and you can translate them into implications an executive will act on. Working across our teams, you will lead workstreams, facilitate workshops, produce the recommendations and materials that carry an engagement from first conversation to a committed program, and take an active role in growing your client relationships. You are comfortable leading conversations with executives, you can turn an ambiguous business problem into a structured point of view on your own, and you hold a high standard for the quality of the work.

Responsibilities

• Build and deepen relationships with C‑suite executives, business leaders, and the leaders of AI, Product, Marketing, Design, and Data teams, and lead strategic conversations about how their organizations build enterprise‑wide AI capability
• Act as a trusted advisor to your clients, leading them through opportunity discovery and managing the day‑to‑day relationship across the life of an engagement
• Develop a deep understanding of each client’s business model, digital operating context, and competitive pressures, and identify where new capability would materially change how their teams perform
• Lead discovery and current‑state assessment across people, process, and technology, and synthesize findings into a clear diagnosis
• Lead the design of target‑state capabilities, digital operating models, and ways of working, and sequence the change into a credible transformation roadmap
• Develop and present our advisory point of view on digital and AI innovation, including how AI is changing products, customer experience, and competitive dynamics within a client’s industry
• Design and facilitate executive workshops and working sessions that produce decisions and momentum
• Own the structure and quality of proposals, executive presentations, business cases, and engagement documentation to a standard a senior client audience expects
• Contribute to BrainStation’s point of view on the AI, digital, and innovation landscape through thought leadership, events, and client conversations

Requirements

• Bachelor’s degree or equivalent professional experience
• 3–6 years of professional experience in a client‑facing role, with direct experience working with enterprise or corporate clients; experience in consulting, strategy, or advisory roles is a plus
• Demonstrated ability to structure complex, ambiguous business problems independently and to develop and defend a clear point of view
• Strong executive presence and communication skills, with a track record of presenting to and advising senior stakeholders
• Experience leading client workshops, discovery sessions, or working sessions
• Excellent attention to detail, strong organizational skills, and the ability to lead multiple workstreams concurrently
• A genuine and current interest in AI, digital technology, and how organizations transform their capabilities and operating models
• Genuine enthusiasm for in‑person work and collaboration; this role follows a hybrid model with four or more days per week in the office
• Willingness to travel globally for client work as required

Perks and Benefits

• Retirement Planning
• Parental Leave Program
• Flexible Working Hours
• Work from Home Flexibility
• Service Recognition Programs
• Socials, Outings & Retreats
• Culture of Learning & Development

About BrainStation

BrainStation is the global leader in AI and digital skills training, trusted by the world’s leading brands and over 40,000 professionals. Established in 2012, BrainStation empowers professionals and leading companies to build essential skills in AI, Data, Design, Marketing, and Product through live, expert‑led training, and partners with organizations to build scalable, enterprise‑wide AI capability.

BrainStation is committed to maintaining a diverse work environment and is proud to be an equal opportunity employer. All qualified applicants, regardless of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status will receive consideration for employment. If you have any accessibility requirements or concerns regarding the hiring process or employment with us, please notify us so we can provide suitable accommodation.

The estimated compensation for this position is $85,000 to $100,000. This is an estimate and a compensation offer will vary based on the applicant’s education, experience, skills, abilities, and alignment with market data.

#LI-Hybrid