Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

Feb 26, 2023 1h 1m 26 insights Episode Page ↗
Annie Pearl, CPO at Calendly, shares insights on building product, including team structure, OKR alignment, and strategic focus. She also discusses Calendly's unique growth story, the transition to sales-led growth, and offers advice on breaking into product management.
Actionable Insights

1. Narrow Product Focus for Impact

Define a clear product strategy by identifying the specific market, segments, and personas to target, which enables product teams to prioritize effectively and deliver amazing value for a focused group rather than average solutions for many.

2. Define Winning Product Strategy

Use a framework like ‘Playing to Win’ to outline winning aspirations, identify where to play (target markets, segments, personas), and determine how to win with that target audience, which inherently clarifies where not to play.

3. Align OKRs Across Company

Ensure OKRs are tightly integrated from company-level objectives down to department-level key results, with clear dependency mapping and cross-functional plans to support the most important objectives.

4. Instill “Focus Wisely” Principle

Embed a core principle like ‘Focus Wisely’ into the company culture and product development process, enabling executives and teams to make difficult ’no’ decisions and prioritize delivering the highest quality product for target customers.

5. Manage Strategic Focus Shift

Implementing a narrower product focus requires a significant cultural shift across people, processes, and product, especially when transitioning from a broad product-led growth model to a more targeted sales-led approach.

6. Allocate Resources by Strategic Horizons

Allocate product resources across different strategic horizons (e.g., Horizon 1 for immediate needs, Horizon 2 for mid-term growth, Horizon 3 for long-term vision) and adjust percentages over time to align with evolving strategic priorities.

7. Commit to Phased Product Planning

Break down product development into distinct phases (discovery, solutioning, build, launch/measure/iterate) and commit to dates only for the work that is immediately within control, avoiding premature commitments for distant projects.

8. Document Multi-Layered Strategy

Maintain a multi-layered strategy documentation system, including a high-level 3-year company strategy (docs/slides), annual product team OKRs (docs/slides), and project-level templates for feature development (e.g., in Confluence).

9. Leverage Sales for Customer Insight

Product teams should view sales and go-to-market teams as a valuable asset for gaining customer empathy and understanding, as they interact with significantly more customers and can provide crucial insights for product decisions.

10. Structure Product Teams by Persona/Problem

Organize product teams around specific personas or problem areas, such as a ‘Core’ team for end-user features and growth, an ‘Enterprise’ team for IT admins and departmental leaders, and a ‘Platform’ team for integrations and APIs.

11. Integrate Product & Design Leadership

Having product and design functions report into a single leader (e.g., CPO) can ensure a more holistic approach to the end-to-end user experience, integrating problem prioritization with solution delivery.

12. Facilitate PM Problem Debate (OPA)

Implement ‘Opportunity/Problem Assessment’ (OPA) meetings where product managers can frequently debate, discuss, and spar with each other on problem spaces, research findings, and solution approaches, fostering open feedback without leadership presence.

13. Conduct Competitive War Gaming

Organize competitive war gaming sessions where teams are assigned to ‘own’ a competitor for a period, immersing themselves in the competitor’s product, conducting SWOT analysis, and presenting insights to inform company strategy.

14. Reinforce Focus Through Documentation

Reinforce the ‘Focus Wisely’ principle through all documentation, templates (e.g., OPA, PRD), and product review processes, consistently prompting teams to identify the target customer, their needs, and how the solution addresses them.

15. Ask “Why” to Build Scalable Solutions

When engaging with customers, focus on asking the right questions to understand the underlying ‘why’ behind their requests, enabling the development of scalable solutions that meet broader customer needs while preserving the end-user experience.

16. Apply Consumer Product Principles

Apply consumer product development principles, such as funnel optimization, building growth as a discipline, and using data and A/B testing for decision-making, even in businesses that blend product-led and sales-led growth.

17. Hire Inbound-Focused Sales Reps Initially

When transitioning from product-led growth (PLG) to sales-led growth (SLG), initially hire sales reps with an inbound-focused background who are adept at working with proactive leads and product-qualified leads (PQLs), rather than heavy outbound hunters.

18. Match Sales Reps to Target Buyer

Ensure early sales hires match the target buyer profile, focusing on those experienced in selling to departmental heads (e.g., head of sales, recruiting) rather than IT or CIOs, as the buyer persona evolves with company scale.

19. Identify Growth Levers from Customer Usage

Continuously observe how customers are using the product to identify organic ‘pull’ towards new use cases (e.g., teams collaborating) that can inform the next major growth curve, rather than solely relying on speculative feature development.

20. Leverage Early Connections for Growth

For early user acquisition, leverage existing connections, even those through contractors building your product, and consider offering a free tier to reduce friction and encourage viral adoption, especially if the product offers a superior experience.

21. Formal Product Management Entry

Consider applying to Associate Product Manager (APM) programs at scaled companies (e.g., Google, Meta) or even smaller, earlier-stage companies. Alternatively, apply directly to junior PM roles via internal job boards if already working in a product-adjacent function.

22. Informal Product Management Entry

Seek opportunities to shadow or partner closely with a product manager, offering to take on some product-related work. Participate in subject matter expert (SME) programs that pair go-to-market functions with product squads. Another path is joining an early-stage startup where roles are often fluid, allowing you to try product management.

23. Cultivate PM Success Traits

To increase chances of transitioning into product management, demonstrate curiosity, passion for the product and solving customer problems, and consider tinkering with side projects to hone PM skills.

24. Discover APM Programs

To find open Associate Product Manager roles, search for ‘Associate Product Manager’ on job boards like Glassdoor.

25. Engage with CPO Support Communities

For Chief Product Officers and product leaders, engage with communities like ‘Skip’ to gather advice, manage challenges, discuss career growth, and network with peers in similar roles. Follow the Skip community on LinkedIn for more information.

26. Send Calendly Without Awkwardness

When sending a Calendly link, first offer the recipient to share their availability or choose a time from your calendar. Additionally, use the ‘add times to email’ feature to reduce friction by embedding available slots directly in the email.