20VC Ramp's Product Playbook How To Hire Product Teams, How to Run Sprints, How to Increase Product Velocity, When and How to Go MultiProduct with Geoff Charles, VP Product @ Ramp

In the latest episode of "20 Product," host Harry Stebbings interviews Jeff Charles, the VP of Product at RAM, revealing insights into product management and innovation in fast-growing companies. Jeff emphasizes the importance of product teams being closely integrated with sales, especially in the early stages, to identify customer pain points and iterate quickly. He shares his journey from management consulting to product management, focusing on customer-centric development and the significance of understanding customer aspirations and challenges. Jeff also discusses hiring strategies, advocating for hiring competitive individuals who are eager to build great products and can quickly adapt to the company's high-velocity culture. Additionally, he offers tactical advice on running efficient two-week sprints, the value of empowering teams to make decisions, and the necessity of aligning product and marketing efforts for successful launches. Jeff's approach underlines the balance between art and science in product development, the critical role of intuition in startups, and the strategic use of AI to enhance product experiences.

• Product teams should be closely involved with sales, especially in early stages.
• The founder or the first product manager is often responsible for securing the first hundred customers.
• Product teams should use the sales process as a means to identify customer pain points.
• Product teams need to be more service-oriented in the beginning, acting almost like professional services.
• Listening to customer feedback during demos and quickly incorporating it into the product can build strong relationships.

"Products should sit with sales and should be in every single sales demo."

This quote emphasizes the importance of product teams being present during sales demonstrations to understand customer reactions and gather feedback.

"Earlier on, the founder or the first product manager should be selling the first hundred customers."

This quote highlights the role of the founder or initial product manager in directly engaging with the first set of customers to sell the product and understand their needs.

"You actually should be like a bit more professional services oriented as a product team."

This quote suggests that product teams should initially focus on tailoring their product to meet specific customer needs, similar to a professional services approach.

• Jeff Charles has experience in management consulting and big data analytics.
• His approach to product management involves getting close to customers and understanding their pain points.
• Building a good relationship with the tech team is crucial for developing technology that addresses customer needs.
• Understanding customer aspirations, habits, and definitions of success is key to identifying their pain points.

"The first energy was management consulting out of college, so it's all the hype around just how to think, how to structure, how to sell."

Jeff Charles explains his initial career focus, which provided him with a foundation in strategic thinking and selling.

"I think the product team kind of came running for there."

This quote describes how Jeff Charles' career naturally progressed into product management due to his close work with customers and technology.

• Spending time with customers and walking in their shoes is crucial for understanding their pain points.
• Product managers should ask open-ended questions to uncover real issues rather than seeking validation for preconceived ideas.
• Watching customers use the product can reveal areas for improvement.
• Product managers should spend less time in the office and more time engaging with customers.

"I think you kind of have to walk in their shoes for a full day."

Jeff Charles stresses the importance of deeply understanding the customer's daily experience to identify their true pain points.

"Oftentimes, like product managers, they have an idea and they ask the question to validate their idea and it's actually the wrong idea."

This quote points out a common mistake where product managers seek confirmation for their ideas rather than genuinely understanding customer needs.

• Identifying what excites you and gives you energy is crucial for career focus.
• It is equally important to recognize what drains your energy and avoid those areas or industries.
• Understanding what you enjoy and what frustrates you can help narrow down career choices.

"Figure out what gets you excited. You do have energy throughout the day. What is that?"

Jeff Charles advises on finding what truly motivates you in your work to guide your career choices.

"What really bothers you. Is it like large meetings? Is it bureaucracy?"

This quote suggests identifying the aspects of work that diminish your energy to steer away from them in your career.

• Hiring the right people is one of the most challenging aspects of building a company.
• Understanding the company's needs is crucial for making good hiring decisions.
• It's important to distinguish the individual's contribution to growth from the company's overall success.
• Hiring more individual contributors (ICs) initially can help validate the company's strategy before bringing on executives.
• The performance of new hires should be assessed within three months to determine if they're a good fit.

"The biggest mistakes were probably on go to market."

Jeff Charles reflects on the difficulty of hiring for go-to-market roles and the importance of understanding the specific needs of the company.

"Don't hire executives that will then hire people under them because that obfuscates a lot of their performance."

This quote advises against hiring senior executives too early, as it can make it difficult to assess their individual performance.

• Growth teams are typically established after achieving product-market fit.
• Determining what to focus on during the pre-product market fit phase is challenging.
• The product should be aligned with sales efforts, and product teams should be involved in sales demos.
• Being aggressive in making it easy for customers to switch to your product is key.
• Two-week sprints can help structure product development efficiently.
• Monday leads meetings and Tuesday team-wide scrum meetings are essential for planning and accountability.

"Products should sit with sales and should be in every single sales demo."

Reiterating the importance of product teams' involvement in sales to understand customer reactions and gather feedback.

"The founder or the first product manager should be selling the first hundred customers."

This quote underscores the role of the founder or initial product manager in customer acquisition and understanding their needs.

"You actually should be like a bit more professional services oriented as a product team."

Jeff Charles advises product teams to focus on tailoring their product to meet specific customer needs, similar to a professional services approach.

• Empowerment is central to the culture, with individuals taking initiative rather than having tasks assigned top-down.
• Social dynamics encourage individuals to take on tasks, especially when their peers are also engaged and their manager is present.
• Publicly posting goals and assignments creates transparency and clarity regarding responsibilities.
• The "scoreboard" approach involves individuals reporting on their achievements and explaining any shortcomings.
• Gratitude is emphasized to foster a supportive culture where team members help each other reach goals.

"If you believe in empowerment, then a lot of it has to come from the individuals." "Here are our goals, and here's who's doing what." "What have you achieved? And the individuals say, I achieved this or I didn't, and here's why."

The quotes highlight the importance of individual agency in task assignment and accountability, with a transparent system that allows for self-reporting on progress and challenges.

• Overemphasis on task management can detract from the main objectives.
• Product managers should avoid becoming project managers who complete tasks for engineers.
• Employees should be encouraged to manage up by communicating their needs, risks, and questions.
• Creating a culture of empowerment and velocity is crucial, and employees should be treated as founders of their own work.
• If an employee is not ambitious enough, it may be necessary to part ways to maintain a high-performance culture.

"Don't write tickets on behalf of people. Like, let them write their own tickets." "Instead, treat them like founders themselves."

The quotes emphasize the need for employees to take ownership of their work and the avoidance of micromanagement, fostering a culture of empowerment and self-direction.

• Every quarter, teams take time to reflect on achievements and set goals for the next three months.
• Offsites focused on customer-centric goals help prevent burnout and encourage continuous improvement.
• This strategic pause allows for reassessment of processes, people, and strategy.

"Every quarter we take a step back and we look at, okay, what do we achieve in the last three months?"

The quote underscores the practice of periodic reflection to maintain focus, prevent burnout, and align the team's efforts with long-term objectives.

• As a company grows, planning shifts from shorter sprints to longer-term goals.
• Different teams, such as customer support, sales, and marketing, require a clearer understanding of the product roadmap.
• Long-term planning enables the creation of aggregated feature sets that can be marketed effectively.

"You need to have a bit more of a longer-term focus or a longer-term goal and plan to make sure that you can address those needs at that stage."

The quote explains the necessity of extending the planning horizon as the company scales to meet the needs of various teams and customers.

• A culture of open feedback and cross-departmental advice helps bridge gaps between teams.
• Transparency and shared goals foster trust and reduce tension between product and marketing.
• Product marketers are involved in user research to better understand and market the product.

"What I mean by that is like if you're a salesperson, you can go into my product spec and leave a comment on my product spec with your opinion."

The quote illustrates the importance of open communication and collaboration between departments to ensure alignment and mutual understanding of goals and strategies.

• Decision-makers must be empowered with data without being slowed down by it.
• Commitment to decisions and alignment on outcomes are essential, even when opinions vary.
• A culture focused on caring about outcomes, not just opinions, is key to maintaining speed.

"You empower the decision maker." "The culture should be, I want to share my opinion because I care about the outcome."

These quotes convey the idea that while input is valuable, it is the decision-maker's responsibility to use it effectively to maintain momentum.

• Prior to product-market fit, build systems with confidence and manage risk appropriately.
• Post-product-market fit, focus on scalability and the potential for reusing systems for new products.
• Planning ahead for future products helps in leveraging existing systems and resources.

"What can I reuse from the first product in terms of the second product?"

This quote highlights the strategic approach of building systems that can be repurposed for future products, maximizing efficiency and scalability.

• Maintain a single-product focus until achieving significant market share.
• An R&D department should explore new features and products without distracting the go-to-market team.
• Introduce new products to the market only when the growth of the initial product slows and there is readiness for expansion.

"Keep a small, small team in the tech organizations building the next product."

The quote advises on keeping a dedicated, small team focused on developing new products while the main go-to-market team remains focused on the current product.

• Start with product-led growth at the bottom of the market to establish a business case for new products.
• Gradually involve the go-to-market team by providing them with proven positioning, use cases, and potential revenue data.
• Cross-selling and scaling occur once the new product has established its market fit.

"We start at the bottom of the market with product-led growth on those products."

The quote outlines a strategy for introducing new products without disrupting the focus of the go-to-market team, allowing for a smooth transition and scaling.

• For larger companies, new product releases are more about marketing to existing customers and the broader market.
• At Ramp's stage, with a substantial customer base, the focus is still on market impact rather than existing customer perception.
• Companies should not be overly cautious about new product releases as the market is forgiving.

"I don't think it matters for larger companies."

The quote suggests that the potential negative impact of a new product release on a company's brand is often overstated and that companies should not be deterred from innovation.

• When launching a new product, it's critical to make a loud entrance in the market.
• Before announcing a product to the market, customers should be on a beta version.
• Marketing strategies should differ for customers and the broader market.
• Having a large Total Addressable Market (TAM) allows for tailored marketing approaches.

"When you go live with a new product, just go as loud as you can in the market."

The quote emphasizes the importance of making a significant impact when introducing a new product to capture the market's attention.

"Your customers should already be probably on a beta before even announce it to the market."

This quote highlights the strategy of engaging customers early in the product development process through beta testing before a public launch.

• OKRs are often overemphasized, leading to a narrow focus on hitting goals without strategic thinking.
• Product strategy should drive success metrics rather than OKRs alone.
• Debates on OKRs can lead to political games within an organization, distracting from the real business objectives.
• Executives should focus on the strategies needed to achieve goals and why those goals matter.

"Ochr is just a way to measure performance, right?"

Jeff Charles clarifies that OKRs are merely performance measurement tools and not strategies.

"But there's no thinking on the exec level around how we can actually achieve that goal and why that goal is important."

Jeff Charles criticizes the lack of strategic thinking at the executive level when using OKRs, suggesting that goals are set without a clear plan for achievement or understanding of their significance.

• Leading metrics should be prioritized over lagging metrics like revenue or market share.
• Leading metrics provide actionable insights for teams to influence outcomes.
• Value-based metrics, such as customer transactions and usage, are preferred as they indicate long-term success.
• Metrics should be actionable within short time frames to be effective.

"I think setting goals on lagging metrics like revenue, market share, nps, that is not going to be clear to a team on how to actually change those metrics."

Jeff Charles explains that goals based on lagging metrics do not offer clear direction for teams on how to affect those metrics.

"The question really is around metric setting is like, can I as a team in a two week sprint, move this metric?"

Jeff Charles emphasizes the importance of choosing metrics that a team can influence in a short period, ensuring they are relevant and motivating.

• Teams should have one or two clear, achievable, and motivational goals.
• Good goals are specific, measurable, and inspire action.
• Bad goals are repetitive and not motivating, resembling vision or mission statements rather than actionable objectives.

"Each team should probably have one, maybe two goals."

Jeff Charles advises that teams should have a limited number of focused goals to maintain clarity and direction.

"A good goal is, it's clear, it's achievable, it's motivational."

Jeff Charles describes the characteristics of an effective goal that drives teams towards success.

• Startups need to clearly define their hypotheses about customers, problems, and solutions.
• Hypotheses should be documented to facilitate reflection and learning from failures.
• A strong hypothesis can lead to successful product development, while a weak or incorrect hypothesis can result in product failure.

"I think oftentimes PM are enamored with their solution and they're not actually good at defining the hypothesis that led them to that solution."

Jeff Charles suggests that product managers often become too attached to their solutions and fail to properly articulate the underlying hypotheses.

"You're a bad pm if you don't learn from your failures and you blame others."

Jeff Charles stresses the importance of learning from mistakes and taking responsibility for the hypotheses made during product development.

• Post mortems should be conducted without blame and with a focus on curiosity and learning.
• They require cross-functional teams to build trust and share perspectives.
• Action items from post mortems should be clear and timely to prevent repeating the same mistakes.

"Blame? Like no blame. I think it's actually like you need to have curiosity, you need to engage with questions, you need to have a fairly cross functional team that everyone that's affected be present so that you build trust with those teams."

Jeff Charles emphasizes the importance of a blame-free, curious approach to post mortems that involves all affected parties to foster trust and learning.

• In-person interactions can build trust, which is crucial for effective teamwork and product reviews.
• Remote work can be as effective as in-person if there is a strong culture of trust within the team.

"Oftentimes, trust is eroded if you don't actually meet in person."

Jeff Charles notes the importance of face-to-face meetings to maintain trust among team members, which is essential for successful collaboration.

• Large companies often struggle to innovate due to short-term board expectations, a single business model, and established team structures.
• Startups may have an advantage in innovation due to their agility and lack of entrenched structures.
• A company's unique positioning should be considered in its product strategy, even in the face of potential competition from larger companies.

"The reality is it's very hard for large companies to actually innovate."

Jeff Charles discusses the challenges large companies face in innovating and launching new products, suggesting that startups may have an advantage in this area.

• The decision to sunset a product should consider the cost of maintenance and the impact on the application's complexity.
• Doubling down on a product requires confidence in the next hypothesis and an assessment of the effort needed to test it.
• If a strong secondary hypothesis is lacking, it is often better not to invest further in the product.

"So at ramp we've shipped a lot of things and I don't think we've been particularly good at taking things down."

Jeff Charles reflects on the challenges of deciding when to sunset features or products that may no longer be beneficial.

• Product development is a blend of art and science, with design playing a significant role in creating a delightful user experience.
• While there are scientific processes in product development, the variability in team performance suggests an artistic element.
• Creativity and design are crucial for developing consumer-like experiences in B2B products.

"I have a standard scientific process for product development that I've tried to apply across the entire teams, and yet different teams perform in very different ways."

Jeff Charles acknowledges that despite having a systematic approach to product development, the outcomes vary, indicating that product development is not solely a scientific endeavor.

"And I think art is a big part of what we do at ramp."

Jeff Charles highlights the importance of the creative aspects of product development, particularly in design and user experience.

• B2B companies and startups often lack data, making intuition or strong ideas crucial in the early stages.
• Startups should hire individuals with strong intuition or ideas that can be quickly tested with qualitative data.
• Product managers from large tech companies may excel in testing and metrics but may lack customer research intuition.
• Hiring should focus on candidates who are critical of software products and understand good product design.

"B two B companies have a lot less data than b to c, and startups have no data."

This quote underscores the scarcity of data in B2B startups, highlighting the importance of intuition in the absence of quantitative data.

"Lean into that, because you're not going to have data for a very long time."

The speaker suggests embracing intuition-driven decisions as startups will not have substantial data to rely on for a significant period.

• AI is expected to reduce the importance of user interfaces (UI) in product design.
• AI can streamline tasks by abstracting data and providing raw intelligence, leading to more dynamic and conversational interfaces.
• The future of software may involve less tactical work and more strategic work due to AI's capabilities.

"AI will most profoundly impact product by reducing the importance of UI."

This quote reflects the belief that AI will simplify product design by making traditional UI elements less critical.

"Software is going to look a lot less like tables, graphs and drop downs, and a lot more like a conversation."

The speaker predicts a shift towards conversational interfaces in software, facilitated by AI's ability to process and present data efficiently.

• The speaker disagrees with the notion that a founder must always lead product development for a company to succeed.
• Founders should focus on vision, brand, and market positioning while empowering product and tech teams to make decisions.
• It is important for founders to maintain high team velocity and provide guidance without micromanaging product details.

"I don't agree. And again, this Shopify, obviously, Toby's very involved in the product surface area at ramp."

Jeff Charles expresses disagreement with the idea that a founder must always be the head of product, citing Shopify as an example where the founder is still involved but not leading product development.

"You need to have an empowered product team and tech team that actually calls the shots in terms of the sequencing."

This quote emphasizes the need for empowered product and technology teams to take the lead on product development decisions.

• To ensure new hires align with the company's focus on velocity, assess their motivation for joining and past experiences pushing projects through.
• Candidates should demonstrate the ability to confront and address obstacles and show a desire to build and ship products quickly.
• Hiring individuals with a "chip on their shoulder," such as former founders or long-time engineers, can contribute to a culture of high velocity.

"How do you hire people that have a strong sense of velocity?"

Jeff Charles discusses the importance of hiring individuals who share the company's emphasis on rapid development and execution.

"Hire people who have sometimes a chip on their shoulder, like people who were ex founders that might not have succeeded or early engineers that have been coding for a long time that just want to build great things."

The speaker suggests that individuals with something to prove or a strong desire to build can be valuable assets in a fast-paced environment.

• The hiring process includes take-home cases related to the company's field but not directly about the company's work to avoid exploiting candidates' efforts.
• Take-home exercises are designed to gauge candidates' work ethic, clarity of thought, and ability to influence a team.
• The hiring process also tests candidates' ability to think deeply on the spot through various case scenarios.

"We do cases that basically are like lateral things, about ramps."

Jeff Charles explains that take-home exercises are relevant to the company's space but not directly about the company's actual projects.

"Are they super clear and are they able to influence a team?"

The quote highlights the importance of clarity and influence in a candidate's ability to work effectively with a product team.

• Overcommunication builds trust between product leaders and the company's leadership team.
• Product leaders should share regular updates on decisions, trade-offs, and areas where leadership input is needed.
• Encouraging the entire team to share their progress and goals promotes transparency and alignment.

"Over communicate? Over communicate? Over communicate."

Jeff Charles advises product leaders to frequently communicate with the leadership team to maintain trust and alignment.

"The first thing everyone on my team tells me, what did they get done last week? What are they going to get done this week?"

This quote demonstrates how regular communication about progress and goals can help maintain team focus and momentum.

• Product leaders should specialize in one area, such as technology, business, or design, to build trust with their team.
• Founders often make the mistake of not letting go of the "how" and not being clear enough about the "what" when hiring product teams.
• It is crucial for founders to micromanage initially, then step back and empower the team once they are confident in their abilities.

"They don't let go in terms of the how, and they're not clear enough in terms of the what."

Jeff Charles identifies common mistakes founders make in hiring and managing product teams, such as micromanaging and lack of clarity.

"Be a super micromanager the first month and signpost that with your hire, and then step off and step out."

The speaker advises founders to be clear about their initial hands-on approach and then to step back to empower their hires.

• Jeff Charles does not aspire to be a CEO, preferring to focus on building products rather than fundraising and marketing.
• He admires Apple's product strategy, which combines craftsmanship, delight, brand loyalty, and a compounding ecosystem effect.
• The speaker emphasizes the importance of a product strategy that continues to innovate and dominate the market, as exemplified by Apple.

"I don't think so. I have very little patience with fundraising, no offense, and I'm not a very strong marketer."

Jeff Charles explains his preference for building products over the CEO role, which often involves fundraising and marketing.

"Apple continues to crush it from a product strategy perspective."

This quote shows the speaker's admiration for Apple's successful product strategy and brand loyalty, which he hopes to emulate at Ramp.

• Running and product management share similarities in their long-term nature, metrics orientation, and the need for repetition to achieve success.
• Setting near-term goals and positive visualization can help overcome challenges in both running and product management.

"It's long and hard. You have to do like short distance as you go to this long distance."

Jeff Charles draws a parallel between the iterative nature of running training and product management sprints.

"Slow down slightly and also just, I think, aim for more near term goals."

The speaker suggests strategies for pushing through difficulties in running, which can also apply to managing challenging product development milestones.