Strategic Programs Lead

Grammarly offers a dynamic hybrid working model for this role. This flexible approach gives team members the best of both worlds: plenty of focus time along with in-person collaboration that helps foster trust, innovation, and a strong team culture.

Grammarly is the trusted AI assistant for communication and productivity, helping over 40 million people and 50,000 organizations do their best work. Companies like Atlassian, Databricks, and Zoom rely on Grammarly to brainstorm, compose, and enhance communication that moves work forward. Grammarly works where you work, integrating seamlessly with over 500,000 applications and websites. Founded in 2009, Grammarly is No. 7 on the Forbes Cloud 100, one of TIME’s 100 Most Influential Companies, one of Fast Company’s Most Innovative Companies in AI, and one of Inc.’s Best Workplaces.

We’re looking for a seasoned Strategic Programs Lead to join our G&A Strategy & Operations team — a high-trust, high-impact role that will partner directly with Ashlee, our Head of G&A Strategy & Ops, to drive some of the most critical people- and change-focused initiatives across the company.

This is not a behind-the-scenes role. You’ll serve as the strategic spine of the org alongside Ashlee, and step in as the primary point of contact during her maternity leave. You’ll run high-stakes programs from end to end, shape org-wide communication strategies, and serve as a consultative advisor to senior leaders and EAs alike. You’ll need to bring both operational rigor and people-savvy instincts — helping create clarity in chaos and momentum in moments of ambiguity.

In this role, you will:

• Lead cross-functional, change-heavy programs with a focus on the People, Legal, and Finance orgs.
• Serve as the primary program partner to Ashlee on strategic initiatives — from early shaping to execution.
• Design internal communications strategies for high-visibility efforts, working closely with our Comms & Execution Partner for rollout.
• Act as a trusted advisor to senior leaders across G&A — helping shape priorities, sequencing, and tradeoffs.
• Provide light-touch coaching and consultation to Executive Assistants on offsite design, team communications, and org-wide alignment.
• Drive calm, clarity, and accountability across complex stakeholder landscapes.

We’re seeking a senior-level operator who blends strategic acumen with emotional intelligence. The ideal candidate will bring:

• 8-10+ years of experience in strategy, operations, or change management — ideally with time in consulting or an internal strategy/Chief of Staff-type role.
• A proven ability to manage high-visibility, cross-functional programs with limited oversight.
• Exceptional stakeholder management skills — able to build trust quickly with senior leaders and influence without authority.
• Clear, crisp communication — especially in moments of ambiguity or tension.
• A systems-thinking mindset with strong judgment on how and when to bring structure.
• Comfort saying “no,” “not yet,” or “yes, but here’s how” — and doing so without damaging relationships.
• Deep organizational awareness, with a high EQ and the instincts of a people whisperer.
• Bonus: experience supporting G&A functions (People, Finance, Legal) or working closely with executive assistants and strategic comms teams.

Grammarly offers all team members competitive pay along with a benefits package encompassing the following and more:

• Excellent health care (including a wide range of medical, dental, vision, mental health, and fertility benefits)
• Disability and life insurance options
• 401(k) and RRSP matching
• Paid parental leave
• Twenty days of paid time off per year, eleven days of paid holidays per year, and unlimited sick days
• Home office stipends
• Caregiver and pet care stipends
• Wellness stipends
• Admission discounts
• Learning and development opportunities

Grammarly takes a market-based approach to compensation, which means base pay may vary depending on your location. Our US locations are categorized into two compensation zones based on proximity to our hub locations.

Base pay may vary considerably depending on job-related knowledge, skills, and experience. The expected salary ranges for this position are outlined below by compensation zone and may be modified in the future.

Zone 1: $197,000 – $271,000/year (USD)

At Grammarly, we value our differences, and we encourage all to apply—especially those whose identities are traditionally underrepresented in tech organizations. We do not discriminate on the basis of race, religion, color, gender expression or identity, sexual orientation, ancestry, national origin, citizenship, age, marital status, veteran status, disability status, political belief, or any other characteristic protected by law. Grammarly is an equal opportunity employer and a participant in the US federal E-Verify program (US). We also abide by the Employment Equity Act (Canada).