Annie Pearl’s Path: Former CPO of Calendly’s Growth Tips

Posts, Building Your Product Career, Growing with Community, Podcast, The Path to CPO

“Choosing the right opportunities that will make you a CPO depend on what type of product management you want to be doing.” -Annie Pearl

By: Oriana Castro Ramirez, Product Leader

In this episode, I had the pleasure of hearing from Annie Pearl, previously the CPO at Calendly, when this episode was recorded. Annie’s impressive product background is diverse. Having worked with Box to the director level and taken it all the way to CPO with Glassdoor and Calendly, you would be surprised to hear that Annie is also a licensed attorney in California! 

Her former role as CPO at Calendly and current role at Microsoft make her an inspiring figure for aspiring product leaders. Join me as I share the key takeaways and insights from this insightful conversation, providing valuable learnings for your career journey.

Before we dive into the key takeaways, let me briefly introduce myself. I’m Oriana Castro Ramirez, a product leader on a quest to reach new heights in my career. Like many of you, I aspire to become a CPO with a product I feel obsessed about someday. Annie’s episode shed light on valuable lessons that resonate deeply with my own aspirations, and I’m thrilled to share them with you.

My 8 favorite takeaways from Annie:

1. Choosing the Right Opportunities

Evaluate potential opportunities based on the type of product management you want to pursue. Consider your skill set, curiosity, and connection with the product. The last one will give you so much information about yourself. Act based on how energized you are to shape the product you’re evaluating. Additionally, assess the stage of the company, as hypergrowth and finding product-market fit offer distinct challenges and excitements.

2. Business Skills

As Annie emphasized, honing your business acumen is crucial for product leadership. Understanding business drivers and thinking through different role lenses lets you align your mindset with the company’s vision and execute strategies effectively.

3. Continuous Learning

While there is an abundance of resources available, it’s essential to focus on areas where you need personal growth. Identify the gaps in your career path and invest your energy in acquiring the specific knowledge and skills to propel you toward your CPO aspirations. Do you still get nervous speaking in front of an audience? Pick a course for it and apply the learnings in your next presentation. Remember that your growth mindset is the most critical setup to get to the CPO level.

4. Alignment with Your Direct Manager

Cultivate a strong career relationship with your manager by maintaining constant and clear communication about where you want to be. Your manager can become your most prominent advocate and guide in your journey. Though luck may play a role, act as if you are the luckiest person in the company, and you might be surprised about how things unravel for you.

5. CEO Expectations

 If you have your sights set on an executive role, ensure that you and your CEO clearly understand the skills and responsibilities associated with being a CPO. Misalignment of expectations can have far-reaching consequences, so it’s essential to establish a shared vision of the value they expect you to bring to the company and the role you will perform for the team.

6. Prepare for Board Meetings

Leverage the premortem technique to anticipate potential challenges and questions that board members may pose. By de-risking your presentations, you demonstrate preparedness and foster confidence in your leadership ability. A premortem is one of my favorite pieces in my product toolkit, so when Annie mentioned how you should do it for your important presentations, it all made sense! Atlassian has a thorough guide for premortems. Use it as a template and simplify the steps to create your pre-meeting plans.

7. People, Processes, and Product

As a product leader, divide your focus into these three distinct spaces. Engage and empower your product team, design processes instead of being at their mercy, and define a compelling product vision that aligns the entire organization.

8. Vision Clarity and Strategy

The primary responsibility of a product leader is to provide a clear vision and a strategy to achieve it. Lack of understanding and alignment within the team can lead to disconnection and ineffective execution. Everyone should understand their contributions and dependencies as clearly as day.


Throughout this podcast episode, Annie delved into several overarching themes and key areas relevant to our collective journey toward becoming CPOs. These include understanding the differences between Vice President (VP) and CPO roles, building effective teams, preparing for board interactions, comprehending CPO responsibilities, embracing personal and professional sacrifices, and anticipating how the role of a CPO will evolve in the future. 

Listen to the episode now so you can take advantage of all tips!

Annie Pearl’s insights from “The Path to CPO” podcast episode offer invaluable guidance for women in product management. We can navigate our careers with greater intention and purpose by incorporating these key takeaways into our journeys. Remember, as you embark on your path to CPO, stay true to yourself, continuously learn and adapt, and seize the opportunities that align with your passions and skill set. The future is bright for women in product, and together, we will shape the leadership landscape.

Discussion Questions

  1. How do you prioritize your career growth and choose the right opportunities in product management?
  2. What are some effective strategies for honing your business acumen as a product leader?
  3. How do you maintain alignment with your direct manager and build a strong career relationship?
  4. Have you ever experienced a misalignment of expectations with your CEO or upper management? How did you address it?
  5. How do you prepare for board meetings to ensure you deliver impactful presentations?
  6. In your experience, how have you balanced the focus on people, processes, and product as a product leader?
  7. What are some effective methods for providing vision clarity and defining a strategy for your team?
  8. How do you navigate the differences between Vice President (VP) and Chief Product Officer (CPO) roles in your career aspirations?
  9. Can you share any personal sacrifices you’ve made in your product management journey and how they have influenced your growth?
  10. How do you foresee the role of a CPO evolving in the future, and what skills do you think will become more critical?

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About the author

Headshot of Oriana Castro Ramirez

Oriana Castro Ramirez

Oriana is a passionate product leader and community leader in Women In Product, dedicated to empowering women in tech and driving social impact through innovative products. With over 12 years of experience driving product innovation, she brings a diverse background as a founder and advertising collaborator with Toyota, Procter & Gamble, and Twitter to bridge gaps and foster innovation in the industry.

Fun fact: Oriana is an avid reader, mental health advocate, and multilingual. Her ultimate dream is to own a farm in the Colombian mountains, where she can raise cows, capybaras and spend Friday nights enjoying RuPaul’s Drag Race with her partner and their pack of weiner dogs.