Head of Strategy

For more detail, see our internal posting here.

The Role

Sawmill is looking for a Head of Strategy to own strategic clarity across the agency.

The short version is this:

We've gotten where we are with a some smarts, a bit of luck, and a ton of grit.

This role exists to reduce chaos, protect margin, and make strong decision-making repeatable. You’ll work alongside leadership to set strategic direction across accounts, define what matters, and prevent scope creep before it reaches execution.

This is not an account management role.

This is not an execution-heavy role.

This is a senior role for someone who is calm under pressure, decisive, and comfortable making hard calls early.

This role requires real fluency in digital and e-commerce performance.

You won’t need to personally run campaigns or build Shopify themes, but you must be able to read analytics confidently, diagnose performance issues across funnel stages, and challenge digital arguments with evidence. If you’ve never been responsible for revenue performance or conversion outcomes, this role is likely not the right fit.

We do our best work together. As a leadership role, candidates must be at the office in Huntsville, Ontario weekly to collaborate in person with the team. Presence matters in this role, particularly during planning, decision-making, and moments where clarity is critical.

About Sawmill

Sawmill sits right at the intersection of commerce and creativity. We build digital experiences that connect people to brands through strategic content, digital marketing, and e-commerce.

We’re a small, senior team that values:

• Clear thinking over busy work
• Long-term client relationships over one-off wins
• Creativity supported by strategy

We work across recurring client partnerships and short-term project engagements, often blending brand, performance, UX, and content into a single system. We move fast, but we don’t move sloppy.

Our Showreel

Who are we looking for?

We’re looking for a strategic leader who:

• Thinks clearly in ambiguous situations
• Understands digital, e-commerce, UX, and conversion deeply
• Knows how to say no early — and explain why
• Protects scope, margin, and team focus
• Can turn messy inputs into simple, actionable plans
• A leader who can communicate their ideas clearly, especially when decisions are uncomfortable

You don’t need to be the loudest person in the room, but when you speak your ideas should consistently land.

What will you be doing?

Lead Strategy

• Own strategic direction across all client accounts
• Define priorities, success metrics, and how something should be done
• Work with clients to define goals, and then translate them into clear, actionable plans
• Identify—with empathy—what matters, and what doesn’t to clients and team members

Lead Digital Marketing & E-commerce

• Lead digital and e-commerce strategy across accounts
• Own UX and conversion thinking, including teardowns, cohort analysis, and opportunity prioritization
• Review performance reporting critically and challenge assumptions before execution begins
• Guide execution through clear direction and prioritization (not micromanagement)

Scope & Margin Protection

• Define scope boundaries per project
• Identify when work becomes a re-scope or new project
• Prevent reactive requests and quick asks
• Flag risks early and clearly

Build Frameworks & Processes

• Build strategic frameworks, playbooks, and planning tools
• Document repeatable decision-making logic
• Turn strong thinking into systems the team can reuse

Proposals & Planning

• Lead proposal strategy, structure, and scope
• Define phasing and pricing logic
• Support the leadership team on sales with strategy, scope, and pricing (not closing deals)

Hiring & Team Support

• Develop a Growth Team of e-commerce and digital marketing executors
• Within your first 30 days, hire and onboard a Digital Marketer
• Provide strategic direction to execution roles
• Ensure execution capacity aligns with strategy

What you will NOT be doing

• You will not be an account manager
• You will not own client satisfaction or sales
• You will not run projects by default
• You will not absorb execution to “help out”
• You will not manage payroll or people ops

If the role drifts into these areas, something has gone wrong.

What do you need?

• Strong strategic judgment and structured thinking
• Deep understanding of digital marketing, UX, and e-commerce
• Experience owning or directly influencing digital revenue outcomes is required
• Comfort making decisions with incomplete information
• Clear written and verbal communication
• Business and revenue awareness
• Ability to collaborate closely with creative and operations leadership
• A bias toward clarity, not complexity

We believe there’s no shortcut to being a good storyteller, but there is a secret to it: you have to live.

Because good storytelling comes from experience. With that in mind, the most necessary things for this role are not accolades or talents. The things you need for this job are the skills, ethics, and empathy you've picked up on your journey to this point.

Qualifications

(You can either have them or convince us why you don't need them.)

• 5+ years in a senior strategy, growth, or digital leadership role
• Experience working directly with clients
• Agency or fast-moving environment experience preferred
• Proven ability to lead strategy without owning execution

What Success Looks Like

30 Days

• Strong understanding of all active accounts
• Scope boundaries clearly defined
• Immediate risks identified
• Digital Marketer hired and onboarded

60 Days

• Full ownership of Tier 2 strategy
• Reduced founder strategic involvement
• New internal frameworks in use
• Improved clarity in client presentations and delivery

90 Days

• Strategy no longer bottlenecks delivery
• Scope creep caught early
• Consistent strategic decision-making across accounts

Performance-Based Profit Sharing

For the Head of Strategy, performance means improving clarity across accounts, protecting margin through early scope definition, and reducing founder dependency on day-to-day strategy.

Success looks like fewer reactive requests, healthier project margins, clearer proposals, and a team that executes with confidence instead of chaos. Profit sharing is tied to these outcomes and reflects the impact strong strategy has on the overall health of the business.

This will be paid out semi-annually. If you are tracking with the expectations, you could earn $20,000 in the year. It will be an open conversation with leadership any time. No BS.

Additional Information

Sawmill is an equal-opportunity employer with a strong commitment to diversity and inclusion. We encourage applications from all qualified individuals and will provide appropriate accommodation for candidates with disabilities or accessibility needs throughout the recruitment process, upon request.

What's next?

We value mutual fit and honest conversation over performative interviews. That’s why we adhere to a three-step interview process where you’ll meet different members of our leadership team and get to have open conversations.

Interview 1: General Manager

Interview 2: Creative Director and Account Manager

Interview 3: Founder

This role includes a 3-month contract period for both sides to confirm fit. We believe this leads to better long-term outcomes for everyone involved.

Send an email to jobs@sawmill.digital if you're interested or have any questions.