Director of Brand & Advocacy

About the Role

Calendly is seeking a strategic and experienced Director of Brand & Advocacy to lead one of the company's most critical marketing functions. Reporting to the Vice President of Brand and Product Marketing, you will own Calendly's comprehensive brand amplification strategy across social media, public relations, communications, and customer advocacy channels. This is a leadership position for a talented executive ready to shape how millions of users discover, understand, and engage with Calendly's brand at scale.

What You'll Own

As Director of Brand & Advocacy, you will be responsible for defining and evolving an integrated brand amplification strategy with a 1–3 year vision. Your strategic priorities will span social media, PR, and advocacy channels to drive awareness, share of voice, and brand affinity. You will translate company and product priorities into coordinated campaigns and programs that make Calendly's story impossible to ignore in the market.

You will lead a talented team consisting of a Social Media Lead, a Customer Advocacy Lead, and a PR Contractor. Your leadership will focus on setting clear goals, providing coaching and development opportunities, creating an environment where each team member excels, and holding the team accountable to measurable outcomes while securing the resources needed for successful execution.

Key Responsibilities

• Brand Strategy & Vision: Define and continuously evolve Calendly's integrated brand amplification strategy. Set a clear 1–3 year vision for how the brand shows up across social, PR, and advocacy channels to grow awareness, market share of voice, and brand affinity among target audiences.
• Team Leadership & Development: Lead, mentor, and develop your direct reports (Social Media Lead, Customer Advocacy Lead, and PR Contractor). Establish clear performance goals, provide ongoing coaching, remove organizational blockers, and advocate for necessary resources and budget allocation.
• Social Media Strategy & Execution: Oversee all social media strategy and day-to-day execution. Partner with the Social Media Lead to develop platform-specific strategies, content pillars, editorial calendars, and channel playbooks that expand reach and drive meaningful engagement with target audiences.
• Public Relations & Media Relations: Guide and provide strategic direction to the PR contractor. Shape Calendly's media narrative, prioritize high-impact media opportunities, ensure consistent brand voice and positioning across earned media placements, and measure PR impact on brand awareness and sentiment.
• Customer Advocacy Programs: Develop and execute customer advocacy initiatives that mobilize Calendly users as authentic brand advocates. Create pathways for customers to share their stories, manage case study development, coordinate customer testimonials, and amplify customer success stories across channels.
• Employee Advocacy & Internal Communications: Serve as a key cross-functional partner to Internal Communications and Employee Experience teams. Help activate employees as authentic brand voices by providing training, content, and encouragement to share company stories within their professional networks.
• Content & Campaign Development: Oversee the creation of compelling brand content and campaigns that feed amplification channels. Ensure all content is audience-first, on-brand, and strategically connected to broader marketing narratives and business objectives.
• Performance Measurement & Analytics: Establish and track KPIs across all brand amplification channels. Provide regular reporting on reach, engagement, sentiment, share of voice, and business impact. Use data to inform strategy optimization and demonstrate ROI of brand and advocacy initiatives.
• Cross-Functional Collaboration: Work closely with product marketing, product management, sales enablement, and corporate communications teams to ensure brand amplification efforts support broader company goals and product launches.

What You Bring to Calendly

The ideal candidate is a strategic marketing leader with 8+ years of experience in brand marketing, corporate communications, social media strategy, or related disciplines. You have demonstrated success leading teams, developing brand strategies at scale, and managing multiple integrated channels simultaneously. You are a storyteller at heart—passionate about crafting narratives that resonate emotionally and drive business results.

You have proven experience managing social media channels for B2B or consumer brands, understanding platform algorithms, audience psychology, and content best practices. You have led or coordinated PR and media relations efforts, with strong relationships in relevant media landscapes. Experience building and scaling customer advocacy or community programs is highly valued.

You are operationally excellent—comfortable managing budgets, tracking metrics, and driving accountability across your team and cross-functional partners. You communicate with clarity and influence, able to distill complex strategies into compelling narratives for both internal and external audiences. You move quickly in a fast-paced environment while maintaining strategic thinking and long-term vision.

Above all, you are authentic and values-driven. You believe in the power of genuine storytelling and customer-centric marketing. You're excited about Calendly's mission and product, and you want to be part of a team that thinks boldly and commits to work that matters.

Why Join Calendly's Marketing Team?

Calendly's Marketing team is responsible for how millions of people globally discover, understand, and fall in love with the Calendly product. The team shapes brand narrative, mobilizes customers and employees as authentic advocates, and drives the awareness and affinity that fuels Calendly's growth. The team moves fast, thinks boldly, and is deeply committed to telling stories that matter—with strong support from leadership and resources to execute at scale.

Working at Calendly means joining a company in the midst of exciting product growth with millions of active users worldwide. You'll accelerate your career to the next level by learning from and collaborating with some of the best marketing and business professionals in the industry. If you want to learn, grow, and do the best work of your life alongside talented colleagues, Calendly offers a fantastic opportunity to advance your professional journey.

💰 Compensation not publicly listed. Market estimate for similar roles: from $200K, varying by experience and location.