Director of Brand & Advocacy

A day in the life of a Director, Brand and Advocacy at Calendly

What's so great about working on Calendly's Marketing team?

We are the team behind how millions of people discover, understand, and fall in love with Calendly. From shaping our brand narrative to mobilizing customers and employees as authentic advocates, our Marketing team drives the awareness and affinity that fuels Calendly's growth. We move fast, think boldly, and are deeply committed to telling stories that matter — and we're looking for a leader to help us do it at scale.

Why do we need you?

We are looking for a Director of Brand and Advocacy who will bring strategic vision, operational excellence, and a genuine passion for brand storytelling to one of our most critical functions. You will report to the Vice President, Brand and Product Marketing and be responsible for owning Calendly's brand amplification strategy across social media, PR and communications, and customer advocacy channels. You will lead a talented team — a Social Media Lead, a Customer Advocacy Lead, and a PR Contractor — and be accountable for both the channel programs that maximize distribution and the compelling content and campaigns that feed them. You will also serve as a key cross-functional partner to our Internal Communications and Employee Experience teams, helping to activate employees as authentic brand voices.

On a typical day, you will:

• Define and evolve Calendly's integrated brand amplification strategy, setting a 1–3 year vision for how we show up across social, PR, and advocacy channels to grow awareness, share of voice, and brand affinity. Translate company and product priorities into coordinated programs that make Calendly's story impossible to ignore.
• Lead and develop your team — a Social Media Lead, Customer Advocacy Lead, and PR Contractor — by setting clear goals, providing coaching, and creating an environment where each person can do their best work. Hold the team accountable to outcomes while removing blockers and advocating for resources needed to execute.
• Oversee Calendly's social media strategy and execution, partnering with the Social Media Lead to develop platform strategies, content pillars, editorial calendars, and channel-specific playbooks that grow reach and drive meaningful engagement. Ensure social content is on-brand, audience-first, and connected to the broader marketing narrative.
• Guide and provide strategic direction to our PR contractor, helping shape Calendly's narrative, prioritize media opportunities, and ensure PR efforts are tightly connected to broader brand and business goals. Serve as the internal voice of the brand in all communications decisions, translating company priorities into clear story angles and messaging frameworks the PR contractor can execute against.
• Build and scale customer advocacy programs that identify, activate, and nurture brand champions — turning customer success into reviews, testimonials, case studies, speaking opportunities, and community engagement that amplify Calendly's story at scale. Design the systems and incentive structures that make participation easy and sustainable.
• Partner with Internal Communications, Employee Experience, and the Social Media Lead to activate employees as authentic brand voices on social and professional networks. Provide strategic direction, content toolkits, and brand guidance that makes it easy for employees to share Calendly's story in ways that feel genuine and impactful.
• Partner cross-functionally with creative, product marketing, demand gen, and executive communications teams to develop compelling content and campaigns that feed all brand and advocacy channels. Ensure creative quality, message consistency, and strong alignment between brand moments and business objectives.
• Establish KPIs and a reporting cadence to measure the impact of brand, PR, and advocacy programs — tracking reach, share of voice, engagement, and pipeline influence. Use data and insights to continuously optimize strategy and communicate program effectiveness to senior leadership.

What do we need from you?

Basic Qualifications

• 15+ years of progressive experience in brand, communications, or marketing roles, with at least 3 years in a director-level or equivalent senior leadership position managing cross-functional teams.
• Demonstrated track record of developing and scaling integrated brand amplification strategies across social media and customer advocacy channels, with the ability to set strategic direction for PR and communications efforts executed by agency or contractor partners.
• Proven experience leading and developing direct reports and contractor/agency relationships, with a strong track record of building high-performing, accountable teams.
• Deep expertise in B2B social media strategy and content development, including platform best practices across LinkedIn, X (Twitter), and other key channels relevant to a SaaS audience.
• Comfort working with and providing strategic guidance to PR contractors or agency partners — able to set messaging direction, prioritize story opportunities, and evaluate PR output without needing to be a hands-on media relations practitioner.
• Experience building or scaling customer advocacy, reference, or community programs — including reviews, testimonials, brand ambassadors, and customer marketing initiatives.
• Data-driven mindset with the ability to establish KPIs, measure program effectiveness across channels, and translate insights into strategic decisions.
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time.

Preferred Qualifications

• Experience in B2B SaaS or technology companies, ideally in a product-led growth environment where brand and advocacy play a key role in the growth flywheel.
• Familiarity with customer advocacy platforms (e.g., Influitive, Khoros, or similar) and community management tools used to manage and scale advocate programs.
• Experience partnering with internal communications or people teams to shape employee-facing brand initiatives, or familiarity with employee advocacy platforms (e.g., EveryoneSocial, Bambu) as a collaborator or sponsor of the program rather than a primary operator.
• Strong existing relationships with B2B technology, productivity, or SaaS media contacts that can be activated for Calendly's benefit.
• Experience launching integrated brand campaigns from concept through execution, including partnering with creative and design resources to develop compelling content.
• Background spanning both in-house and agency environments, with a strong understanding of how to set clear scopes of work and get the most from contracted relationships.