Title

Board director at Wiley (NYSE: WLY), Root (NASDAQ: ROOT), Fandom, RTS, and Bridge Legal.

Founders Should Call Me When

I’m here to help with product-related questions or concerns, growing pains/challenges, and making tough decisions about resource allocations when faced with too many (or too few) potential options for investment.

Background

Prior to focusing on board service, I served as chief operating officer at PlayFab, the SaaS backend platform for online games. During my time as COO, PlayFab was a Series A Madrona portfolio company experiencing 10% month-on-month user growth; PlayFab was acquired by Microsoft in 2018. Prior to PlayFab, I served as senior vice president of product at GrubHub, the market-leading pioneer in online food delivery, during its progress from a growth stage startup with $20M in revenues to a $2B public company. Earlier in my career, I served in a variety of roles at Expedia, most recently as VP of product and connectivity, where I played a key role in the successful transformation of Expedia’s air ticket business model and fulfillment technology in the face of rapidly changing market conditions.

Superpower

Partnering with senior leadership to bring an end-user product perspective to help drive a company’s strategy. I’ve worked with high-growth and mature B2C/B2B and marketplace businesses to help companies use customer empathy to identify and focus on key initiatives and effectively leverage their unique set of capabilities.

Lessons Learned

Experience breaking down large, risky initiatives into no-regrets phases, using experimentation to drive learning, and using (often incomplete) data to drive decision-making.

Title

Co-founder and former VP of product management at Smartsheet, current product advisor for Meetingflow, TerraClear, Truebase, Uplevel, and Zync.

Founders Should Call Me When

You’re overthinking it and aren’t sure whether to trust your gut instinct. Oh, and call me if you want to avoid a bunch of the many mistakes I’ve made.

Background

I spent 20+ years helping two startups go from 0 to $100M+ in revenue and then navigate successful IPOs. The first was a traditional enterprise sales model, and the second, Smartsheet, was a product-led growth SaaS model. At Smartsheet, I wore many hats in the early days as a co-founder, but my main role was building out the product management and UX design teams. In those early days of SaaS, there was a lot of trial and error as we learned in many painful ways how dependent the business was on the product UX and onboarding flows. After building new muscles for online marketing to individuals and teams, self-service try-and-buy product workflows, and templatized solutions, it was time to circle back around and figure out how to meet the many different requirements for selling enterprise deals.

Superpower

Finding product/market fit, building early product teams, and balancing infrastructure, end-user feature, and go-to-market priorities.

Lessons Learned

UX is always important, pricing is difficult, A/B testing is worth the effort, and hiring a person who’s just OK for a hard-to-fill position is bad for morale.

Title

CMO at Forter. Former VP of marketing at VMWare, Heptio (acquired by VMware), Tintri (TNTRQ), and Merced (acquired by NICE Systems).

Founders Should Call Me When

They want to dig into the metrics that hold marketing accountable and when they need tough love on overly complicated positioning. Marketing is a broad discipline that includes product marketing, demand, growth, communications, events, customer and partner, and more. Let’s talk about where your first head of marketing (or marketing team) needs to be strongest.

Background

I’m a zero-fluff marketing leader who has worked across industries and stages and intentionally led product marketing, demand gen, and brand at different stops on my journey. At Forter (joined at Series E), we up-leveled the story from point solution to platform and built an ultra-efficient enterprise marketing machine. Today, $1 of marketing spend produces $19 of qualified pipeline. At Heptio (joined as first marketer/employee #40, Series A), we built our credibility with a thoughtful approach to the cloud-native community and our pipeline from $0 to $27M in ~6 months. When VMware acquired Heptio, I led marketing for the Cloud Native division with a team of 110 marketers driving a $700M+ business. At Tintri (joined at Series C), we grew revenue 3x in three years, which led to a rollercoaster IPO. At Merced (joined, then immediately acquired by NICE Systems), we defined a category with/through key analysts and established our leadership position.

Superpowers

Stripping messaging back to its core. Building a marketing dashboard that a Board of Directors understands and cares about.

Lessons Learned

It’s important that founders/leaders see Marketing as a strategic function. Early investment in marketing ensures that Sales is well-fed (with qualified pipeline) as they grow. It’s hard for marketing to catch up if Sales has been scaled and marketing has been neglected. Plus, a great marketing team can help you see around corners with competitive insight and market opportunity analysis, and they should be able to forecast your bookings six months ahead.

Title

Corporate VP at Microsoft, board member at eBay, former CPO at Robinhood, VP at Google, and an angel investor.

Background

Throughout my career in the tech industry, I have been at the cutting edge of technology used to solve customer problems at scale. I started my career at Akamai, the world’s first internet content delivery network. At Google, I led efforts across search, YouTube, and Google Now, the precursor to Google Assistant. As the technical advisor to the CEO, I worked on company-wide strategy, particularly on AI and conversational assistants. I founded the AR and visual search product Google Lens, which helps you search what you see, driving notable growth in search use.

As chief product officer at Robinhood, I helped evolve the company beyond trading into saving and long-term investing, with retirement products for Gen Z.

I serve on the board of eBay and, as part of the audit and the tech committees, guide the management on AI and tech initiatives that can drive impact for the business. I served on the board of Capital One and advised the management team on tech and product initiatives such as the early adoption of cloud and AI.

Superpower

My strength lies in my ability to marry complex technological advancements, especially in AI and machine learning, with intuitive user experiences and zero-to-one products.

Lessons Learned

Why NOW is as important to get right as WHY. This is a lesson I learned while building personal conversational assistant products — way before LLMs and NLP improvements.

Founders Should Call Me When

They are evaluating product use cases, exploring product market fit, and hiring and scaling engineering and product teams.

Title

Senior vice president and chief information security officer for the Oracle SaaS Cloud Security engineering and operations organization.

Founders Should Call Me When

I am here to help founders understand how to overcome security and compliance challenges or blockers occurring with an enterprise CSO/CISO and also how to best engage and connect with CISOs in the enterprise. I can also provide guidance on the best security controls to implement and drive to ensure successful security, audit, and compliance of the startup as it grows through the various phases.

Background

Previously, I built the public cloud security engineering organization as a director in the Google Security and Privacy organization for three years, and his preceding 18 years were spent with Microsoft in numerous security platform, cloud, product and engineering leadership roles. One major change at Microsoft I specifically championed was the strategic shift to a subscription model and technology investments that drove the Threat Management Gateway (TMG) annual product line revenue to increase significantly (50% annually) with a lead from $80M ARR to $150M in just two short years. At Google, I led the holistic Google Cloud Security organization development from an internal expert infrastructure team of 20 to a 160+ DevSecOps organization that released four major external public launches in less than 3 years. I’m also a venture partner with Rain Capital VC with a successful track record that includes notable acquisitions, starting with my seed investment and cloud enterprise advisor of Twistlock, which was acquired by Palo Alto Networks in less than 4 years. I have continued my informal angel and VC investment and advisory engagements with numerous startups in the early and growth phases prior to later mature finding stages. I also have been the sole advisor and initial seed investor in Step-Security, which has organically connected to 1,200 public open-source projects and achieved viral growth with 4,000+ workflows in almost all major technology companies in less than 2 years.

Superpowers

1. All amazing visions and strategies require phenomenal execution. I continue to build and leverage my military training to have a clear mission target and always deliver completing that mission as planned every time.
2. Winning enterprise customers mandate not just understanding the enterprise, infrastructure, culture, and technologies, it is about seamless integration into that environmental graph. I connect the dots between innovative security technologies with the existing business infrastructure, policies, and requirements to rapidly identify and integrate new solutions that were not previously perceived as possible.

Lessons Learned

1. A communication structure and rhythm consistency internally and externally to ensure connections and community growth.
2. An external personality presence and associated awareness are critical to bringing attention and engagement to a new or unknown company, business, or solution.
3. Enterprise customer culture and knowledge are paramount to win and enter the traditional large-scale business environment.

Founders Should Call Me When

I am here to help founders understand how to overcome security and compliance challenges or blockers occurring with an enterprise CSO/CISO and also how to best engage and connect with CISOs in the enterprise. I can also provide guidance on the best security controls to implement and drive to ensure successful security, audit, and compliance of the startup as it grows through the various phases.

Title

Chief customer officer of Conversica and formerly a post-sales Sr. executive at Outreach and DocuSign.

Founders Should Call Me When:

They’re considering what roles to invest in post-sales — whether it be services, account management, customer success managers, support, or others. Also, if they are considering what channels to support in terms of customer communication and/or how to design for a low-touch model. Additionally, if they are working through the customer experience design and considering how to structure responsibilities across all GTM teams, compensation alignment, reporting, KPIs, and otherwise how to measure success.

Background

Over the past 25 years, I’ve built post-sales organizations and designed customer experience for high-growth companies that pioneer new markets. Leading customer success, support, and operations at companies like DocuSign and Oureach.io, I’ve transformed organizations to support the business from $50M to north of $500M and IPO. In my most recent role as chief customer officer at Conversica, I helped pivot their focus from SMB to global enterprise customers interested in adopting AI. These innovative companies gave me hands-on experience crafting playbook growth, retention, and scalability strategies for digital platforms, serving millions and Fortune 100 enterprises.

Superpower

Building world-class post-sales organizations and operations that feed the customer voice directly into product and GTM strategies. Measured through clear metrics, the resulting flywheel impacts revenue growth acceleration, retention, and insight on where to invest for scale.

Lessons Learned

Through all of these great experiences, I’ve learned it’s critical to name the North Star and then structure the organization, communications, systems, and tools to achieve it. The clearer you are, the faster you can go. A key part of that clarity is deep listening to your customers and a company-wide willingness to act on what they ask. For a startup, it might be easy for sales to turn their chair to talk to the developer. But as you grow, that has to be part of your DNA — making sure the entire company is instrumented to hear, learn from, prioritize, and act on the customer experience.

Title

Chief revenue officer at Launch Darkly and former revenue leader with Forter, Heptio (acquired by VMWare), and Cloudera.

Founders Should Call Me When

They’re debating sales hiring profiles, pressure testing pitch decks/positioning, contemplating appropriate processes as they scale, customer segmentation models, and compensation models.

Background

I’ve led VC-backed sales organizations with diverse starting points over the past 15+ years — ranging from sub $1M to $200M+ ARR. Joining at various funding stages has granted me broad exposure to a wide range of GTM activities — from initial pitch deck creation to implementing rigorous process and enablement strategies as part of pre-IPO ramp up. With sales leadership roles at Cloudera, Heptio, Forter, and now Launch Darkly, I’ve been fortunate to witness explosive growth across data, infrastructure, and now AI/ML domains.

Superpower

Product/competitive positioning, inspiring, and scaling (high-velocity recruiting & process improvement).

Lessons Learned

In the beginning, it’s about customer acquisition (even if it means for free or at low prices) and establishing an effective feedback loop between them and your product organization. Once you’ve demonstrated value and effectively published it, you’re better positioned to replicate that success with credibility. Pay close attention to why you win and lose so you can canonize the learnings across the organization and drive continuous improvement. Lastly, while “Field of Dreams” was a great movie, you can rarely expect that “if you build it, they will come.” It’s critical to devise a balanced inbound/outbound demand generation strategy that you can, ideally, augment with PLG to lessen the inertia of trying your product and self-subscribing.

Title

Board member for BabyList and Getty Images (NASDAQ: GETY) and the former CFO at Rover.

Founders Should Call Me When

You’re looking for a sounding board or help with modeling out future opportunities; you’re brainstorming what execs and staff to hire as the company scales; you need help in reviewing or designing your fundraising deck, selecting bankers, or prepping the company for a go-public process.

Background

I’ve served as CFO of multiple VC-backed companies, ranging from $25M to $200M+ of ARR and >$1B of GMV, allowing me to develop my expertise in designing multi-year business, capital allocation, and fundraising strategies as well as scaling global finance organizations. With my CFO roles at Rover Group, Rightside, and UIEvolution (now Xevo), I bring expertise in the design and operations of high-performing financial organizations that can support all stages of a company from Series B through IPO and beyond.

Superpower

Designing the finance and people organizational structure, including what level of leaders are needed, for each stage of the company’s life — from Series B to multibillion-dollar public company.

Lessons Learned

Your forecasts and plans will be wrong, but it’s okay to pivot. No one expects perfection or for you to have all of the answers. But, they do expect you to be thoughtful around strategy and communicative about status and challenges. It’s all about frequent and honest communication with your investors, your team, and your board.

Title

Advisor | investor | CPTO at Mason and former CTO at Qualtrics

Founders Should Call Me When

You are 1) looking for advice on how to shape and create an R&D organizational structure to support growth in your business. 2) Evaluating leadership profiles. 3) Introducing new disciplines into the business. 4) Assessing the effectiveness of your existing engineering team processes. And 5) facing operational challenges with your product and/or platform.

Background

I’ve been an engineering leader for the last 20+ years at both large public companies and pre-IPO VC-backed startups. Most recently, I was the CTO at Qualtrics, where I was responsible for designing, building, and operating the XM Platform. In my eight years, I re-architected a single-product monolithic PHP architecture into a modern SaaS platform that supported multiple product lines and a monetized robust developer and partner ecosystem that supports 20k+ customers. I grew and scaled the organization from 100 to 1,500, building the information security, internal systems, IT, services engineering, and program management functions while the business grew from $100M to $1.5B in ARR, ultimately resulting in an IPO in 2021. Prior to Qualtrics, I spent 10 years at Amazon in a wide variety of roles, most recently as a founding member and head of engineering for Alexa. There, I grew that team from 0 to 235 in 3.5 years and shipped the first version of Amazon Echo. Prior to Amazon, I was an engineer and engineering lead at Microsoft, Active Voice Corporation, and Openwave systems.

Superpower

I’m at my best when a company has found product-market fit and needs to scale a single-product focused engineering team (roughly 30 FTEs) into a global, multi-disciplinary R&D organization (500+ FTEs). I’ve led multiple engineering teams on transformations where they have re-architected monolithic platforms and scaled their systems to support 10x usage. I’ve built out multiple program management functions that are focused on solving hard, cross-functional operational challenges (e.g., availability, latency, and efficiency of SaaS platforms). I’ve worked across platforms and products and have designed platforms that support multiple independent product lines several times in my career.

Lessons Learned

Scaling an organization requires prescience and adaptability in almost equal parts. I’ve learned that I need to plot a course to an imagined future state but also be able to pivot when new facts or circumstances inevitably arise.

Title

CMO at Zendesk

Founders Should Call Me When

You’ve developed an amazing product but are grappling with how best to build a strong brand, position your solution to customers, price & package your offerings, or recruit a high-impact marketing organization.

Background

I’ve led marketing organizations for SaaS products ranging from $10M to $20B+ of ARR over the past 20 years, enabling me to develop insights and expertise across the full marketing funnel, including brand marketing, demand generation, performance marketing, partner marketing, analyst and public relations, sales enablement, and pricing & packaging. With marketing leadership roles at Google, Qualtrics, Microsoft, and now Zendesk, I’ve had the opportunity to help teams find product-market fit, incubate, and ultimately scale their offerings across consumer, SMB, and enterprise market segments.

Superpower

Brand positioning, product messaging, pricing & packaging, and scaling teams.

Lessons Learned

You can go faster alone but further together. Taking the time to create clarity for your leadership team and communicate your top priorities to the broader organization on a regular basis is critical to achieving long-term success in your business. As your organization and business grow, the need for clarity and alignment increases exponentially.