20Product Calendly CPO Annie Pearl on Why All PLG Companies Eventually Need to Embrace Enterprise, Why it is Easier to Scale into Enterprise than Visa Versa and the Calendly PLG Playbook; What Works and What Does Not

Summary Notes


In a candid conversation with Harry Stebbings, Annie Pearl, CPO at Calendly, delves into the nuances of product management and scaling product teams. Annie shares her journey from aspiring lawyer to product leadership, emphasizing the importance of focus in early-stage startups to achieve product-market fit. She discusses the strategic shift from a horizontal to a vertical approach as Calendly evolved, targeting specific user cases within organizations, and the eventual expansion to address the entire meeting lifecycle. Annie also touches on the challenges of integrating a Product-Led Growth (PLG) model with enterprise sales, the timing of such a transition, and the balance between innovation and executing a solid product strategy. She advises on hiring product leaders and managers, stressing the need for alignment with company growth stages and fostering a culture of innovation. Additionally, Annie reflects on learning from past product strategy missteps, the impact of competition on product decisions, and her admiration for Slack's strategy in transforming business communication.

Summary Notes

Introduction to the Podcast Episode

  • The episode focuses on scaling product and product teams with insights from Annie Pearl, CPO at Calendly.
  • Calendly is a scheduling platform with over 10 million users and 500 companies.
  • Annie Pearl has a background in leading product teams at Glassdoor and Box.
  • The episode includes contributions from Ted Blosser, Tope (Calendly's CEO), and Adam Draper.

"Welcome back to another very special 20 product episode. This is the monthly episode where we sit down with one of the leading product minds to discuss scaling both product and product teams, sharing their tips, tactics and experiences."

"And today I'm super excited to welcome Annie Pearl, CPO at Calendly, the company that makes scheduling meetings simple and painless."

The introduction sets the stage for a discussion on product scaling with a focus on Annie Pearl's expertise and background.

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These quotes introduce sponsored products that align with the podcast's theme of product development and user experience.

Annie Pearl's Background and Entry into Startups

  • Annie Pearl originally intended to become a lawyer but shifted to technology and startups.
  • Her first role in product management was with Expert Financial.
  • She emphasizes the importance of focus in the early stages of finding product-market fit.

"So started my career off actually intending to be a lawyer, and while I was in law school, I actually worked for a management consulting firm and we specialized in working with startups."

"That's really how I got into product management."

Annie Pearl discusses her unexpected transition from law to product management in the tech industry.

The Importance of Focus in Early-Stage Startups

  • Startups should concentrate on solving a single problem exceptionally well.
  • Diversifying too early can lead to a loss of focus and hinder finding product-market fit.

"Just how important it is to kind of maniacally focus on solving one problem and solving it better than any alternative on the market super quickly."

This quote highlights the critical nature of focus in the initial stages of a startup.

Identifying the Right Problem to Solve

  • Startups should identify the most acute pain points in the market.
  • Founders often get distracted by new ideas instead of sticking to their core problem.

"You really want to focus on finding where's the sort of most acute visceral pain points that someone might have within some sort of problem space or some sort of market."

Annie Pearl advises startups to target the most significant pain points in their market.

Knowing When to Develop a Second Product

  • The right time for a second product is after achieving product-market fit with the first.
  • Companies should be cautious not to wait too long to develop a second product.

"I think you get to a place with your first product where it's very clear that you found product market fit."

The quote stresses the importance of having a strong product-market fit before considering additional products.

Relationship Between First and Second Products

  • Second products often leverage the first product's success.
  • There should be a strategic connection between products to increase the likelihood of success.

"I think usually they happen to be pretty well tied together. I don't think it has to be the case, but more often than not, I think there's a reason your second product relies on your first product to become successful."

Annie Pearl discusses how the first product can create advantages for launching a second product.

Calendly's Product Evolution

  • Calendly started with a broad use case and is now focusing on specific customer needs.
  • The company plans to expand into managing the entire meeting lifecycle.

"We really started off as this very horizontal scheduling automation platform... Where we're actually transitioning to now, and have been for quite some time, is going deeper into these sort of use cases where you have really strong product market fit."

Annie Pearl outlines Calendly's evolution from a broad platform to a more focused solution for specific use cases.

Product-Led Growth to Verticalized Sales Approach

  • Starting horizontally allows for 80% functionality across verticals.
  • Calendly strategically decides which additional vertical-specific features to develop.

"So when you think about starting off horizontally, 80% of the functionality we have today will solve the use cases of those departmental users."

The quote explains the benefits of Calendly's horizontal beginnings when expanding into vertical markets.

The Necessity of Embracing Enterprise for PLG Companies

  • PLG companies eventually need to target larger teams and organizations for sustained growth.
  • Direct selling complements PLG by enabling wall-to-wall deployments within organizations.

"You see every iconic PLG company, whether it's slack or Dropbox or Asana or Zoom, at some point they have to add on that sort of direct selling motion to complement the PLG business."

Annie Pearl discusses why successful PLG companies inevitably move towards enterprise sales.

Timing the Move to Enterprise

  • Moving into enterprise sales too early can be detrimental.
  • Companies should look for clear signals of readiness, such as customer pull, before making the transition.

"Going too early can be detrimental, right? Hiring a bunch of salespeople and not having the product or market ready for that motion can be really tough on a business."

The quote cautions against premature expansion into enterprise sales, highlighting the importance of market readiness.

Timing for Sales Team Expansion

  • The expansion of a sales team should be timed with actual demand to avoid inefficiencies.
  • Usage data is a key indicator for the right time to expand the sales team.
  • Patterns in usage data can signal when there is enough user engagement to justify sales team expansion.
  • Organizations must assess their readiness both in terms of market demand and internal organizational preparedness.

"So definitely want to be very careful around making sure you're timing it right."

This quote emphasizes the importance of careful consideration when deciding the timing for expanding a sales team, highlighting that it should align with actual demand.

"One of the pulling mechanisms you see really is in usage data."

The speaker indicates that usage data serves as an important indicator for determining the appropriate time to increase the size of a sales team.

Complexity in Organizational Transition

  • Transitioning from a product-led growth (PLG) to an enterprise model increases complexity across the organization.
  • Product development shifts from focusing on individual users to considering teams, departmental admins, and IT buyers.
  • Sales teams may transition from inbound to outbound strategies, and customer experience (CX) teams evolve from reactive support to managed accounts.
  • Cross-department dependencies become more pronounced, necessitating better integration and communication.
  • Organizations face multiple priorities and must balance the focus between PLG and enterprise sales motions.

"At the highest level, there's just an increased complexity that sort of happens across the whole organization."

This quote summarizes the overall increase in complexity when an organization shifts focus from PLG to enterprise, affecting various departments.

Product Management in an Enterprise Context

  • Transitioning to enterprise involves both "blocking and tackling" for security and compliance as well as more dynamic product development.
  • Product managers must consider interdepartmental value creation and complex use cases when serving larger organizations.
  • The shift from individual to collaborative team use cases presents more interesting challenges for product managers.

"I think there's two answers to that question."

This quote introduces the dual nature of the challenges when managing products for enterprise customers, involving both foundational security tasks and more complex product development.

Prioritization and Executive Alignment

  • Prioritization is a significant challenge when layering enterprise onto a PLG motion.
  • Executive alignment is critical to ensure clarity and direction for the organization.
  • Decisions must be made regarding the balance of investment between PLG growth and enterprise sales development.

"The most important and the biggest challenge the organizations face is not having that alignment at the executive level."

The speaker stresses the necessity of executive alignment to set clear priorities and directions for the organization during the transition to enterprise sales.

PLG and Enterprise Strategies

  • PLG allows for efficient business growth with excellent unit economics, potentially delaying the need for a large sales and marketing team.
  • Scaling up to enterprise from PLG is generally easier than scaling down from enterprise to self-service models.
  • Rules of engagement can become complex when transitioning from an enterprise to a PLG model.

"It's much harder to scale down than it is to scale up."

This quote highlights the relative difficulty of transitioning from an enterprise-focused business model to a PLG model compared to the opposite direction.

Product Marketing in PLG

  • Product marketing in a PLG context is less about traditional marketing and more about the product's inherent value and user-driven growth.
  • As companies scale and target different market segments, the role of product marketing becomes more critical.
  • Product marketing evolves to encompass positioning and addressing the needs of various buyer segments as the company moves upmarket.

"The beauty of the PLG business is that it enables you to build a highly profitable engine."

The speaker describes the advantages of a PLG model, emphasizing its profitability and the organic growth it can facilitate.

The Role of Product Management

  • Product management involves prioritizing the right problems to solve and building effective solutions.
  • The ultimate goal of product management is to deliver impact to the business.
  • Product managers must balance the art of creativity with the science of data-driven decision-making.

"It's all about prioritization. You have limited resources and the job of a product manager is to make sure that you're working on the most impactful things for the business."

This quote defines the essence of product management as the prioritization of resources to maximize business impact.

Art and Science in Product Management

  • Product management combines both art and science, with science aiding in prioritization and art playing a role in solution design.
  • The "art" aspect involves creativity and intuition, which are less teachable than the data-driven "science" of product management.

"Science, therefore, I think, is very heavily influencing that part of product management when it comes to then how do we build a winning product solution."

This quote illustrates the scientific approach to identifying opportunities in product management, while also acknowledging the artistic elements involved in solution design.

Hiring a CPO or Head of Product

  • The need for a product leader aligns with a company's growth trajectory.
  • Founders often handle product management pre-market fit, but as the company grows, the need for a dedicated product leader emerges.
  • A product leader's role evolves from executing a founder's vision to creating predictability and opening up new growth levers.

"Pre product market fit. Founders usually doing most of the product management, working with, directly with the engineers, getting things built."

This quote describes the early stage of a startup where the founder is deeply involved in product management, indicating a later stage for hiring a dedicated product leader.

Role of a Chief Product Officer (CPO)

  • The introduction of a CPO is common in a company's evolution when complexity increases.
  • CPOs are expected to have experience in hiring great product teams and working in complex environments.
  • The timing for bringing in a CPO is critical for the company's growth and product development.

"That's where you typically see someone bringing in a CPO, someone who's seen the movie play out before, hired great product teams able to work in a really complex environment."

This quote emphasizes the typical point in a company's lifecycle when a CPO is brought on board, highlighting their experience and ability to navigate complex situations.

Types of Product Leaders

  • There are different profiles of CPOs, such as visionaries, craftspeople, and operators.
  • Visionaries foresee the future, craftspeople craft products in unique ways, and operators focus on process repeatability.
  • A concern is whether the creativity and artistry in product management are lost as teams scale.

"Visionaries early really kind of foresee the future craftspeople who really kind of crafted in different ways. And then there's operators."

This quote categorizes CPOs into three distinct types, each with their own approach to product management and their unique contributions to a company's product strategy.

Creativity and Artistry vs. Scale in Product Management

  • Creativity and artistry do not have to be sacrificed for scale in product management.
  • The relationship between the CPO and the CEO/founder is crucial, especially in understanding the roles each will play in product development.
  • Hiring decisions should be made based on the complementarity of skills and clarity of roles between the CEO/founder and the CPO.

"Absolutely not. And the best product companies out there find a way not to."

This quote asserts that the best product companies maintain creativity and artistry even as they scale, suggesting that it is possible to balance both.

Hiring Process for Product Teams

  • The hiring process should begin with defining the core competencies required for product managers.
  • A structured hiring process includes a hiring manager phone screen, panel interviews, and a clear evaluation of competencies.
  • The hiring process should be tailored to the company's specific needs and the role being filled.

"How do I literally structure a hiring process? How do you do it today, and what do you want to get out of each subsequent meeting?"

This question leads to an explanation of the structured hiring process for product teams, emphasizing the importance of defining competencies and having a clear evaluation method.

Core Competencies for Product Managers

  • Four main competencies for product managers are strategy, product sense, leadership/communication/execution, and analytical thinking.
  • These competencies help product managers prioritize problems, craft compelling product solutions, inspire teams, and set success metrics.
  • Product managers must be adaptable and capable of iterating on their work to achieve the desired impact.

"The first is really all about sort of synthesizing large amounts of information and data points and being able to use that to prioritize the right problems to solve?"

This quote outlines the first core competency for product managers, focusing on their ability to synthesize information and prioritize effectively.

Testing for Strategic Thinking

  • Testing for strategic thinking involves assessing how candidates prioritize and create frameworks for decision-making.
  • Candidates can be evaluated based on their past experiences or through hypothetical scenarios.
  • The goal is to understand how candidates would approach product strategy within the target market.

"How do I test for strategy and their ability to be a strategic thinker within product?"

This question prompts a discussion on how to evaluate a candidate's strategic thinking capabilities, which is crucial for determining their fit for a product management role.

Presentation Phase in Hiring

  • Candidates should be given clear guidelines on time investment for presentations.
  • Presentations should focus on real problems relevant to the business to evaluate how candidates would approach them.
  • The presentation phase is also an opportunity for candidates to assess if the problems they will work on align with their interests.

"I think it's really important to be clear with candidates how much time you want them to spend on these presentations."

This quote underscores the importance of setting clear expectations for candidates regarding the time they should invest in preparing their presentations.

Common Hiring Mistakes

  • Misalignment between the needs of the company and the skill set of the hired leader can lead to hiring mistakes.
  • Founders must be honest and explicit about what they are optimizing for in a leader.
  • Product managers must be compatible with the company's stage of growth to avoid misalignment.

"Yeah, I think on the leader side, some of the things we've already touched on around just sort of misalignment around what the needs."

This quote points out that hiring mistakes often stem from a misalignment between the company's needs and the leader's skills.

Skills for Early Career Product Managers

  • Early career product managers should focus on core PM fundamentals.
  • These fundamentals include problem prioritization, product sense, communication, storytelling, and analytical thinking.
  • Mastery of these skills is essential for career progression in product management.

"I think at the very beginning, it's all about those core PM fundamentals."

This quote emphasizes the importance of core product management skills for individuals at the beginning of their career in the field.

Career Advancement in Product Management

  • Advancement in product management involves increased complexity and autonomy.
  • Early-stage product managers focus on execution and delivering value.
  • As product managers progress, they transition to owning strategy and execution.
  • Higher positions require managing larger scopes and more complex problems.

"I think the first is you have to do those same things, but with a larger scope and with more complexity and do it with more autonomy."

This quote emphasizes the growth in responsibility and the need for autonomy as product managers climb the career ladder, highlighting the shift from execution to strategic roles.

Resource Allocation Strategies

  • Resource allocation depends on the company's growth stage.
  • Pre-product market fit stage focuses on achieving product market fit.
  • Post-product market fit requires scaling and making processes repeatable.
  • Resource allocation should align with the company's growth curve and product strategy.
  • Innovation culture is crucial to maintain as a company scales.

"If you are pre product market fit, your only job is to get to product market fit."

This quote underlines the primary focus for companies in the early stages of development, indicating the importance of achieving a product-market fit before other considerations.

Product Strategy and Evaluation

  • Product vision and strategy should have a two to three-year horizon.
  • Strategy should be reevaluated quarterly without frequent changes.
  • Data, market, competition, and user mix should inform strategy checks.

"I think a good time horizon for the combination of the product vision and strategy is, call it two to three years."

This quote suggests a reasonable timeframe for executing a product strategy, with the need for periodic reevaluation to ensure it remains on track.

Competitor Influence on Product Strategy

  • Learning from competitors is important, but focus should remain on customers and users.
  • Adherence to a clear product strategy is key unless competitors prompt a strategic reevaluation.
  • Competitors' features should not dictate product decisions if they don't align with the strategy.

"Unless there's something our competition is doing that should make us materially doubt our strategy, I think we will gain far more by maniacally focusing on what we believe we need to do."

This quote advises against reacting to competitors' actions unless they fundamentally challenge the company's product strategy, emphasizing focus on the company's own objectives.

Learning from Product Mistakes

  • Introducing a new product in a company with a successful core product takes time.
  • Sales teams may need incentives to sell new products over established ones.
  • Realistic expectations and integration into the sales motion are crucial for new product success.

"You can't just build a product and launch it and expect that the business is going to be there."

This quote reflects on the lesson learned from a product launch that did not initially meet revenue projections, stressing the importance of go-to-market strategy and sales team incentives.

Product Leadership and Starting a New Role

  • Treat a new role like managing a product, with a clear impact goal for the first year.
  • Create a roadmap for the first 90 days, first half, and second half to achieve the year-end impact.

"What is the impact that you ultimately want to deliver after your first year and kind of work backwards from there to create a roadmap."

This quote advises new product leaders to plan their impact and actions in advance, treating their role development as they would a product's lifecycle.

Diversifying Product Management

  • Encourages transitions into product management from other disciplines.
  • Diversity of thought from various backgrounds benefits product solutions.

"I would love to see more folks transition into product management from other disciplines."

This quote emphasizes the value of diverse experiences in product management, advocating for internal mobility from different areas of an organization.

Admiration for Other Product Strategies

  • Slack's strategy to replace email communication is impressive.
  • Successful execution on a clear strategy can lead to significant industry changes.

"I've been pretty impressed by how well Slack has been able to execute on sort of their strategy to ultimately sort of remove a lot of communication that maybe traditionally would have happened through email."

This quote highlights Slack as an example of a company that has effectively realized its product strategy, achieving a significant shift in communication habits.

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