Dave Fleischman

Fractional CPO | Board Member | Executive Consultant

St. Jude Children's Research Hospital - ALSAC · Issaquah, WA

May 2025 – Present(1 yr)

Along with advisory board work, consultant scaling the CEO in multiple CXO areas including, AI strategy modernization, performance marketing, software lifecyle, scale, strategy, and culture. All work is mission driven to raise money for the hospital.

Chief Product Officer

Angi

Feb 2023 – Apr 2025(2 yrs 3 mos)

Executive leader responsible for product management, analytics, design, research and content for Angi. Responsible for product strategy and delivery, I was part of the team that refocused Angi on an evidence based, data-driven approach that put customer needs, both pros and homeowners, at the center of our work. Additionally, revamped the product delivery cadence to be predictable and focused. • Re-wrote the Angi product strategy in my first ninety days, to focus on customer needs rather than growth at all costs • Along with engineering leadership, delivered a new platform that simplifies the development and scaling of Angi’s experience across multiple brands and page types that will accelerate growth • Reestablished Angi’s leadership in home improvement content and scalability resulting in millions of new high quality pages to help homeowners • Improved the pro experience leading to significant improvements in pro retention (number not published) in my first year and continuing • Conceived of and delivered an AI/LLM driven, custom built interface based upon Angi’s long history of helping homeowners and pros. Second version is in progress. • Homeowner NPS improved over 80% by building customer centric experiences and a relentless focus on solving pain points and bad experiences. • Improved SEO landing page conversion by over 75% and reduced bounce rate by 25% • Revamped the planning process with a focus on backlog stability and reducing churn • Hired and managed a team of multiple VPs and SVPs across product, analytics and design

Senior Vice President Of Product Management

Compass · Seattle, Washington, United States

Feb 2021 – Oct 2022(1 yr 9 mos)

Senior product leader accountable for the core platform and customer-facing product management teams, including incepting and driving the first end-to-end real estate platform in the world that delivers more than $6 billion in revenue. Within the first six months, drove delivery of a new organizational structure that brought engineering, design and product together based on customer-backward workflows. • Within one year substantially improved platform engagement of active agents by 50%. • Hired and grew the product team from 100 to 250, managing up to 150 on teams ranging from core search, to AI, including myriad new customer-facing experiences and managed several VPs and senior directors. • Created the core “rhythm of the business” for Compass, moving from a sporadic planning process to a predictable, team-empowering process, and wrote the first thesis in Compass history. • Led companywide strategic planning for a 1,500-person product and engineering organization based on both customer need and business need, and drove CSAT up by 50% in one year. • Teams delivered several strategic projects that are planned to drive more than $500 million in incremental revenue over three years. • Improved SEO traffic by 30% within six months of investment in the program.

Chief Growth Officer

Blue Nile

Sep 2019 – Feb 2021(1 yr 6 mos)

Responsible for unifying and leading engineering, performance marketing, product management and user experience with a singular purpose to grow Blue Nile. Reshaped the planning and delivery of end-to-end customer experiences from offsite marketing, through post purchase communications delivering high growth and exceptional business results. • Rebuilt the performance marketing team from the ground up and turned around a multi-year annual decline in traffic to mid-double-digit growth in traffic and transactions. • Moved the engineering team from vertical speciality, slow delivery group into a full agile, pod-based group building off a centralized strategy with bottoms-up delivery control. This change happened during the Covid lockdown and within six months • Delivered on a centralized profile and marketing system that unified profiles across Blue Nile and improved email results by over 100% and grew paid traffic via Google by over 100% • Built an algorithm/ML team that launched several over-10%-conversion winning changes with patentable designs • Led the company through the business-critical lockdown of 2020 with a hyper focus on customer benefiting features and business impacting priorities • Hired several leaders including a CTO, head of product, and several VPs of marketing

Chief Product Officer

Blue Nile · Greater Seattle Area

Oct 2017 – Sep 2019(2 yrs)

Executive leader responsible for setting and executing a renewed vision for Bluenile.com and the Blue Nile experience. As part of this effort, built the first product management team in Blue NIle's history and established a data-driven and scientific methodology including major contributions to marketing. Responsible for the technical roadmap, user experience team and for establishing a modern customer experience • Exponentially grew the test and learn capabilities of Blue Nile, via a new testing method, growing from 7 tests in 2017 to well over 100 in 2018 • Improved mobile conversion rate over 50% year on year, overall conversion by 20% • Reversed a major SEO decline, improving incoming traffic by 35% • Presented to the board of directors on a regular basis, including successfully pitching a new customer-centric vision for Blue Nile. • Established a modern software and product management methodology that integrates UX, technology, functional experts and product management. • Envisioned and planned (in development) a systematic customer profiling and marketing system unifying the experience across marketing, customer support, and site. This brings together CDP, DMP, and CRM strategies. • Led a team that filed several provisional patents for Blue Nile around a new machine learning algorithm for recommending diamonds • Integrated and managed multiple strategic vendors in order to renew Blue Nile.

Vice President, Global Product

Expedia, Inc. · Bellevue, WA

Mar 2014 – Oct 2017(3 yrs 8 mos)

Cross-functional leader focused on unifying a product strategy for growth across product and marketing channels worldwide. Work in partnership with marketing, retail and technology to deliver globally-recognized travel brands such as Expedia, Orbitz, Travelocity and eBookers. Primary focus is global products for hotel shopping, flights supply and shopping, Scratchpad, SEO/SEM landing pages and marketing products. • Sustained 15%+ growth in the air product over 3 consecutive years, positioning Expedia Inc. as the largest flight online travel agency in the world. • Lead 50 product managers who set direction for a global workforce of over 1,000 engineers, marketers and designers. • Established content supply system linking together offsite and onsite travel shopper's journey. • Worked with marketing teams to create a system for programmatic advertising, dynamic targeted emails and dynamic advertising. • Represented Expedia with nationally-known publications (New York Times, The Economist, etc.) • Part the leadership team producing "Expedia Product Academy" with high-profile guest speakers and build trainings on product science, deep analytics and product strategy programs used consistently within and outside of Expedia.

Senior Director, Global Product

Expedia, Inc. · Bellevue, WA

Oct 2011 – Mar 2014(2 yrs 6 mos)

Part of a turnaround team focused on renewing the operational model. Established high-efficiency software process, clear direction and product plans, metrics-based product planning, and revived culture of innovation. Responsible for the flights, insurance and Scratchpad products. • Turned around flights product, transforming negative bookings to double-digit booking growth. • Released 400% more A/B tests over the previous year with a 40% win rate. • Within one year, envisioned, funded and released ScratchPad a new big data feature to simplify travel shopping. ScratchPad won significant press coverage, i.e. New York Times, etc. • Redesigned flights product for first time in six years, increasing product performance by over 15%. • Introduced industry-first Flight Recommendations based on customer travel shopping patterns. • Established new business model for flights product that helped fund increased development. • Built strong international teams around positive learning culture.

Senior Director, Technology

Expedia, Inc. · Bellevue, WA

Feb 2011 – Oct 2011(9 mos)

Managed a technology migration from 10-year-old proprietary platform to open source SOA platform, enabling consistent desktop web, mobile web and web application experiences. • Led technology team of more than 70 people, including technical product development, project management, release management and live site management teams. • Introduced methodologies for design-driven development with focus on user experience and delivery of quality over quantity. • Transitioned to Agile methodology with weekly vs. monthly releases.

Group Program Manager

Microsoft · Bellevue, WA

Jun 2009 – Mar 2011(1 yr 10 mos)

Led major company-wide redesign and upgrade of live systems supporting more than $3B in digital content across all Microsoft platforms including all Xbox games, transitioning all content to streamlined new platform. Project saved more than $100 million over 3 years through increased efficiency and reduced error rates. • Headed development of streamlined new platform that reduced content onboard time from 1 year+ to less than 3 months, realized 40% efficiency gain, and supported projected 200% annual growth in overall system capacity. • Created new software development strategy, combining experiences at Apple, Nokia & Microsoft, and drove long-term release strategy. • Managed and grew a team of fifteen program managers and user experience designers.

Head of Program Management

Nokia · Redmond, WA

May 2008 – Jun 2009(1 yr 2 mos)

Reshaped Share on Ovi service to focus on personal media sharing and social networking, growing user base of the service from 100K to more than 5 million unique users. Turned around development team to deliver on-time releases, improved user experience and tighter integration into Nokia suite of services. • Established effective engineering processes and empowered teams to deliver. • Delivered 7 major website updates and 2 Nokia phone client releases used in more than 40 million Nokia phones. Shipped all releases on time despite budget cuts, pay freezes and layoffs, motivating through focus, one-on-one management and incentive-based rewards. • Drove full site user experience overhaul, focusing on simplicity and clean design. • Managed diverse international team of employees and vendors in Finland, U.S. and England.

Engineering Program Manager

Apple Inc. · Cupertino, CA

Jan 2007 – May 2008(1 yr 5 mos)

Led development of all iPhone applications built by Apple for initial iPhone release. Following the iPhone release, served as project lead for first major feature release of the iPhone, first iPod touch rollout, and launch of iTunes. • Worked directly with Apple Human Interface team to design user interaction modes for applications on the iPhone and iPod touch including the wifi music store and iTunes movie rentals. • Program manager for the built in applications on the iPhone such as music, mail, Safari, messages, etc. • Filed for 10 software patents, mostly related to iTunes user interaction and iPhone/iPod touch carrier activation. Patent filing details below. • Drove overall enterprise strategy for iPhone and iPod touch, resulting in iPhone implementation still in use today. • Presented to senior VPs of several Apple divisions. Prepared demos for Steve Jobs and Apple executive staff.

Program Manager, eHome Division

Microsoft · Redmond, WA

Apr 2004 – Jan 2007(2 yrs 10 mos)

Managed design and release of several features for Windows Media Center; drove business strategies. Led Sustained Engineering effort in eHome Division, implementing processes and practices for quality, accountability and customer responsiveness. Led final version of Windows XP Media Center Edition. • Created new strategy and process for Windows Media Center’s Online Media feature that increased performance 10X and surpassed usability standards. • Monetized previously-flat portions of the online product, enabling new business model. * Filed 5 software patents around presenting Internet media in a 10” interface. • Noted expert and requested speaker at several conferences, including WinHec and Digital Life.

Project Manager, Developer Division

Microsoft · Bellevue, WA

Jul 2000 – Apr 2004(3 yrs 10 mos)

Wide range of responsibilities, including feature ownership, deployment, build, release and scheduling. Managed internal and external partner relationships for Microsoft Visual Studio, the company's flagship developer tools platform.

Computer Services Manager, Contractor

Various · Redmond, WA

Jun 1995 – Jun 2000(5 yrs 1 mo)

Various positions including manager of the Redmond WA Kinkos computer department, marketing and educational layout/design and contracting at Microsoft in a build lab, internal site development and help file development.