20VC Lessons From Scaling Trulia to IPO, How To Maximise Your Impact within Your Organisation and Why No One Is Ever 100% Ready For The Next Job with Heather Fernandez, Founder @ CEO @ Solv

In this episode of "20 Minutes VC," Harry Stebbings interviews Heather Fernandez, the founder and CEO of Solve, a startup providing accessible last-minute healthcare. Fernandez has impressively raised over $23 million from top-tier investors like Bill Gurley and Pete Flint. Her diverse background includes pivotal roles at Trulia, Morgan Stanley, and as Senator John McCain's deputy press secretary during his 2000 presidential campaign. Additionally, she serves on the board of Atlassian. The conversation delves into her non-linear career path, the importance of culture and constructive candor in a company, and the challenges of scaling a business. Heather emphasizes the significance of trust, transparency, and leveraging board management for company growth. She also discusses the balance of handling multiple responsibilities and the future aspirations for Solve to simplify healthcare experiences for consumers.

• Heather Fernandez is the founder and CEO of Solve, a startup that provides access to high-quality, last-minute healthcare.
• She has raised over $23 million in funding from notable venture capitalists.
• Heather has a diverse background, with experience in politics, PR, Apple, Morgan Stanley, and was part of the early team at Trulia.
• She also served as the national deputy press secretary for Senator John McCain's 2000 presidential campaign.
• Heather is a board member at Atlassian and was introduced to the show by Pete Flint at NFX and Layla Sturdy at Capital G.

"And so I'm thrilled to welcome Heather Fernandez, founder and CEO at Solve, the startup that simplifies everyday healthcare by providing access to high-quality last-minute care."

This quote introduces Heather Fernandez and her current venture, Solve, highlighting its mission to simplify healthcare access.

"Prior to solve, Heather was part of the early team at Trulia, where she led advertising, product marketing and sales strategy and saw the team go from 20 people through to the $2.5 billion acquisition by Zillow Group."

This quote provides background on Heather's professional journey, emphasizing her significant role in Trulia's growth and success.

• Heather's career began in politics, notably with John McCain's presidential campaign.
• She has worked in various fields, including PR at Apple and finance at Morgan Stanley.
• Heather joined Trulia in 2006, contributing significantly to its growth before its acquisition by Zillow.
• After Trulia, Heather decided to tackle the healthcare industry with the CTO of Trulia, founding Solve to empower consumers in their healthcare experiences.

"In fact, I started my career in politics, where I was on John McCain's 2000 presidential campaign...then ultimately I found my way over to Trulia back in 2006...Once we finished that journey with the sale to Zillow in February of '15, I thought, I think I want to go do that again, but this time in healthcare."

This quote outlines Heather's diverse career path leading up to her decision to start Solve, highlighting her drive to take on new challenges.

• Heather was the first pregnant woman at Trulia, setting an example for work-life balance.
• She drew inspiration from Sami Inkinen's (Trulia co-founder) unapologetic dedication to his Ironman training.
• Heather applied this unapologetic attitude to her role as a working mother, becoming a role model for other women at Trulia.

"I was the first woman to be pregnant at Trulia...I actually think it was Sami's unapologeticness about his hobby and his fitness that made me unapologetic about being that person at Trulia and then being that example to other women who would come after me."

This quote reflects Heather's realization that personal commitments, such as motherhood, can coexist with professional success, inspired by her colleague's approach to his athletic pursuits.

• Heather witnessed Trulia's growth from a small team to a large company with significant revenue.
• She learned the importance of balancing internal growth with external expertise to maintain company culture and manage scaling challenges.
• Heather challenges the notion that management teams need to be reinvented every few years, arguing against blanket statements and for the potential longevity of team members.

"What it takes for a leadership team to scale from roughly a dozen people to 1000, and the combination of growing people internally to maintain that culture and core of the company, as well as bringing in that external expertise."

This quote summarizes Heather's insight on scaling a company, emphasizing the need for a mix of internal development and external expertise.

"Well, I think anyone who makes blanket statements is generally going to be wrong."

This quote is Heather's response to the idea of regularly reinventing management teams, suggesting that there is no one-size-fits-all approach.

• Scaling leadership within a company is possible from early stages to successful public company.
• Amy Butinski's career progression at Zillow exemplifies this, moving from PR to CMO and then COO.
• Some individuals thrive in early-stage startups but may not be driven to scale to the next level.
• The right people should be in place at the right time, matching their skills and passion with the company's needs.

"Amy Butinski, started as the woman in charge of PR, went on to become the CMO of Zillow, and then now is the COO of the Zillow group."

This quote highlights Amy Butinski's career growth within Zillow, showcasing that it's possible for individuals to scale their leadership roles as the company grows.

"And then certainly there are people who, based on their skills or frankly, their interest, are right for a period in time."

The relevance of this quote is in acknowledging that not everyone is suited for every stage of a company's growth, and that's acceptable.

• Culture is likened to a company's operating manual, outlining core principles applicable in all situations.
• Culture varies from company to company and should reflect the unique vision and goals of the organization.
• Constructive candor is highlighted as a core value, combining trust with direct communication to avoid misunderstandings and move quickly as a company.

"I think of culture a bit as an operating manual of a company, sort of the core principles which are true in all situations."

This quote defines culture as the fundamental principles that guide a company's operations, emphasizing its importance in all contexts.

"We think of constructive candor as trust, and this is important. Plus, direct communication is winning."

Here, Heather Fernandez explains 'constructive candor' as a culture value that combines trust with clear communication, suggesting it's a formula for success.

• Authenticity to founders is crucial when building a company's value statement or culture.
• Trust should be the foundation of team interactions, and this should be vetted during interviews.
• Building trust involves creating opportunities for team members to connect outside of work-related tasks.
• Solve organizes company offsites and team events to foster trust and rapport among team members.

"I think there is one. It has to be authentic to your founders."

This quote emphasizes the importance of authenticity in a company's cultural values, starting with the founders.

"We build that into the cadence of our culture."

Heather Fernandez explains that structured events and interactions are deliberately incorporated into the company's routine to build trust and rapport among team members.

• In early stages, startups may face the risk of a false negative due to small data sets.
• Stubbornness can be beneficial in adhering to a company's vision despite limited initial metrics.
• Qualitative validation and looking at various data points are necessary for early-stage validation.
• Startups should not rely solely on A/B testing due to the potential insignificance of early data.

"You really do run the risk of a false negative in the early days because the numbers are so small."

The quote addresses the challenge startups face when interpreting data, as small sample sizes can lead to misleading conclusions.

"You need to look at your validation not just through that a b test and that number that you're seeing on your dashboard today, but from a number of data points."

Heather Fernandez suggests that startups should consider multiple sources of validation beyond just A/B testing metrics.

• Marketplaces must monitor both supply and demand sides.
• On the supply side, volume and operational levers are important.
• On the demand side, top-line numbers and core actions (e.g., bookings for Solve) are critical.
• Day-to-day engagement and success metrics are closely watched to assess company performance.

"We look at both sides. One is on our supply side. We look at volume."

This quote underscores the necessity of monitoring supply metrics in a marketplace business model.

"The core action for solve is the booking."

Heather Fernandez identifies the key action that Solve focuses on, indicating what drives their demand-side metrics.

• Balancing the needs of supply and demand sides in a marketplace is a continuous challenge.
• One side may always be less content, requiring careful management to maintain equilibrium.
• Experience from Trulia and Solve informs strategies for managing marketplace dynamics.

"I love that comment from Leah. Actually, when you think about a marketplace balancing your supply and your demand side, the needs that they have as users, frankly, your internal organization, which..."

Heather Fernandez agrees with the notion that in marketplaces, it's difficult to keep both sides equally satisfied, highlighting the complexity of operating such a business model.

• Building a marketplace involves addressing the needs of both supply and demand sides.
• It's common to experience frustration from either side, but it's not always one-sided.
• Harry Stebbings highlights the inherent challenges and enjoyment in balancing a marketplace.
• Heather Fernandez discusses trade-offs and the importance of internal leadership in understanding and prioritizing the needs of each side to maintain balance.
• Trulia and Zillow's approach to serving consumers ultimately benefited the supply side by growing an engaged audience for agents.

"And it's part of what makes it so damn hard and so damn fun when it comes to building a marketplace, I think it is true that there will always be frustration on some side of your marketplace."

This quote emphasizes the difficulty and excitement in managing a marketplace and acknowledges that frustration is inevitable on either side.

"So if you take the Trulia and Zillow use case, ultimately what we realize as a company is that if we were helping consumers make better decisions... that would best serve the supply side of that marketplace, which was the agent, because we would grow the audience and those agents would have more engaged consumers to transact with."

Heather Fernandez explains how focusing on consumer decision-making can indirectly benefit the supply side by creating a larger, more engaged customer base for agents.

• Heather Fernandez took on a role when an executive hire didn't work out, not out of boldness but necessity.
• Confidence developed over time through understanding that no one starts out knowing everything.
• She advises that people, especially women and underrepresented groups, should take opportunities even if they don't feel 100% ready.
• The misconception of false competence is assigned to people in roles, which can be misleading.

"The reality is people who are in these roles start by not knowing what the hell they're doing, right? And they figure it out piece by piece."

Heather Fernandez shares her realization that everyone starts with a lack of knowledge and gains confidence as they learn and grow in their roles.

"Know that you're never going to be 100% ready, but neither is the other guy. So just take a leap."

This quote is advice from Heather Fernandez, encouraging individuals to take chances and step into roles even if they don't feel fully prepared.

• Companies are likened to growing organisms that require different things at various stages.
• Heather Fernandez uses a framework for hiring based on company size: creators (0-10), teams (10-50), and infrastructure (50-100).
• The first hires are crucial as they set the company culture.
• As the company grows, the need for management and infrastructure increases to maintain efficiency and performance.

"So the first zero to ten people, those are your creators... As you go, call it ten to 50 people, I think of teams... And then when I think about 50 to 100 people, I think about infrastructure."

Heather Fernandez outlines the stages of team development in a growing company, emphasizing the roles and needs at each stage.

• Not everyone finds all stages of a company's growth enjoyable or interesting.
• Heather Fernandez assesses potential team members by understanding what drives them and brings them joy.
• She advises against joining a startup or founding one if the person's motivations align more with scale and impact rather than the challenges of early-stage growth.

"I often have folks who've come in very successful from organizations that have scaled and they have the allure of startup... But I think sitting in a boat in the middle of the ocean... it just does not seem like that would be fun for you."

Heather Fernandez describes how she helps individuals understand whether they are suited for the startup environment based on their motivations and preferences.

• Deciding when to scale is a significant challenge for startups, especially those with funding.
• It's important to look for signals from paying customers on the supply side, like demand for more services and positive core metrics.
• On the demand side, focus on users completing core actions rather than just user growth.
• Heather Fernandez agrees with Sarah Tavill's framework of emphasizing the growth of users completing a core action.

"Having money doesn't necessarily mean that you should be spending a ton of money... I think when it comes to your supply, I think it's critical to look for signals from your paying customers."

Heather Fernandez discusses the importance of responsible spending and looking for customer signals before deciding to scale the business.

"Don't focus on user growth, which can be cheap, but focus on growth of users, completing a core action."

This quote references Sarah Tavill's advice on prioritizing meaningful engagement over mere user numbers when considering scaling efforts.

• Identifying the core action that signifies value creation within a product.
• Recognizing when consumers or users start to engage in that core action as a signal for readiness to scale.
• Importance of understanding the core action to gauge the right time for business expansion.

If you know what your core action is, and your consumers or users are starting to take it, then I would take that as a signal that you're ready to pour some gas.

This quote highlights the significance of identifying a core action that users engage in, which indicates the product is providing value and the business may be ready to scale up.

• The value of simultaneously managing a company's board and sitting on the board of another company.
• Gaining perspective on common challenges faced by companies at different stages.
• Learning from the experiences of larger, successful companies like Atlassian.
• Using insights from board participation to improve one's own board management skills.

It's a tremendously valuable experience to be both the CEO of a company managing a board, and then sit on the board of directors for another company, and especially one as exceptional as Atlassian.

Heather Fernandez discusses the benefits she gains from her dual role as both a CEO and a board member, emphasizing the valuable perspective and management insights it provides.

• The importance of honesty and transparency in managing a board.
• Utilizing the board for its full value rather than just presenting to it.
• Learning from the example of Atlassian's co-CEOs and their approach to board management.

They're incredibly humble and transparent with their board, clearly outlining their perspective, asking us to directly challenge them across core issues facing the company.

Heather Fernandez emphasizes the effectiveness of Atlassian's co-CEOs in managing their board through humility and transparency, setting an example for her own leadership.

• The significance of historical political understanding in current times.
• The impact of recognizing the exclusion of women from historical narratives.

It's the american political tradition by Richard Hofstudter.

Heather Fernandez shares her favorite book, which provides insight into America's intellectual foundations and the historical omission of women.

• The trust equation as a tool for managing teams, resolving conflict, and engaging with customers.
• The components of the trust equation: credibility, reliability, accessibility, and self-interest.

Trust equals credibility plus reliability plus accessibility. Over the denominator is self-interest.

Heather Fernandez describes the trust equation, which she frequently considers in her professional interactions to build and manage trust.

• The productivity hack of living without regrets to focus on future actions.
• Avoiding the waste of time associated with dwelling on past mistakes.

My biggest productivity hack is I have no regrets.

Heather Fernandez shares her approach to productivity, which involves not dwelling on past errors and instead focusing on the next steps.

• Disagreement with the notion that multitasking is ineffective.
• Recognition of the necessity of multitasking in certain roles, such as being a mother and CEO.

The one that causes me to roll my eyes the most profoundly is that multitasking is ineffective.

Heather Fernandez expresses her disagreement with the common advice against multitasking, citing her own experiences as a counterargument.

• The strategy of taking a moment to breathe and gain clarity during stressful situations.
• Teaching her children the same technique for dealing with challenges.

I do what I've taught my kids to do, which is I look up at the sky and I do that either on a short walk or I look out the window from my office and I take deep breaths and I give myself a little bit of space.

Heather Fernandez discusses her method for dealing with crisis moments, which involves stepping back and taking deep breaths to clear her mind.

• The goal of simplifying healthcare experiences for consumers.
• The anticipation of making a significant impact on day-to-day healthcare.

My five year roadmap is to make it easier for the consumer to solve it today in their day to day healthcare experience.

Heather Fernandez outlines her vision for the next five years at Solve, focusing on improving healthcare experiences for consumers.

• Acknowledgment of the valuable insights shared by Heather Fernandez.
• Promotion of the League dating app and its high standards.
• Endorsement of Zoom for video and web conferencing.
• Recommendation of Culture Amp for employee feedback and company culture enhancement.

Such exciting times ahead for Heather and for solve and I couldn't be prouder to have Heather on the show.

Harry Stebbings concludes the show by expressing excitement for Heather Fernandez's future endeavors and recommending various services to the audience.