[Hiring] Director, Brand Influence, Advocacy & AI Discovery @Calendly

September 14, 2026

Role Description

We are looking for a Director of Brand Influence, Advocacy & AI Discovery to define how Calendly builds trust, authority, and discoverability in an AI-first world. You will own Calendly's customer advocacy strategy and key distribution channels (social and PR/Communications), while expanding the function to include AI-powered discovery, ensuring customer voices, community engagement, reviews, thought leadership, and trusted third-party validation strengthen how buyers—and increasingly AI platforms like ChatGPT, Gemini, Claude, Perplexity, and Microsoft Copilot—discover and recommend Calendly’s new and existing products.

On a typical day, you will:

Define and execute Calendly's long-term customer advocacy and AI discovery strategy.
Define and manage channel roadmaps for social media and PR/Communications.
Build and scale customer advocacy programs including reviews, references, testimonials, ambassadors, speakers, referrals, and creator programs.
Develop a customer evidence engine that transforms customer success into trusted digital assets including reviews, user-generated content, tutorials, community discussions, and executive advocacy.
Partner with Growth, SEO, and Content teams to advance Answer Engine Optimization (AEO) and Generative Engine Optimization (GEO).
Increase Calendly's visibility across AI-powered discovery platforms including ChatGPT, Gemini, Claude, Perplexity, and Microsoft Copilot.
Expand Calendly's presence across review sites (ie, G2, Trustradius), Reddit, LinkedIn, YouTube, podcasts, industry communities, and partner ecosystems.
Lead employee and executive advocacy initiatives that amplify authentic brand voices.
Partner with Product Marketing, Growth Marketing, Product, Customer Success, and Lifecycle Marketing to support product launches, adoption, and expansion.
Lead, coach, and develop the advocacy, social, and PR team while establishing clear operating rhythms and measurable outcomes.
Measure performance using traditional channel-specific metrics alongside emerging AI discovery metrics.

Qualifications

12+ years of experience in Brand Marketing, Customer Marketing, Community, Product Marketing, Growth Marketing, or Customer Advocacy.
Experience building and scaling advocacy or community programs within a B2B SaaS organization.
Strong understanding of Product-Led Growth (PLG) and customer-led growth strategies.
Experience building programs from 0→1 while scaling mature functions.
Exceptional cross-functional leadership and executive communication skills.
Strong analytical mindset with experience defining KPIs and measuring business impact.

Requirements

Experience in a high-growth B2B SaaS company ($100M+ ARR preferred).
Knowledge of AI-powered search ecosystems and emerging Answer Engine Optimization (AEO) and Generative Engine Optimization (GEO), including relevant software solutions for tracking.
Experience partnering with SEO, Organic Growth, Content Strategy, and Product Marketing teams.
Experience with advocacy platforms such as Influitive, Gainsight, Khoros, or similar.
Experience leveraging review platforms, online communities, creator ecosystems, and third-party trust signals to drive growth.

Success Metrics

Customer participation and advocacy engagement.
Review quality and velocity across G2 and other review sites.
Brand share of voice and sentiment.
AI recommendation share and AI citation frequency.
Growth in trusted third-party mentions.
Customer-generated content growth.
Community engagement and digital authority.

Benefits

Base salary is just one component of Calendly’s total rewards package.
All full-time (30 hours/week) employees are also eligible for our Top Performer Bonus program (or Sales incentive), equity awards, and competitive benefits.

Back to blog

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...