Rachel Wolan
Chief Product Officer at Webflow
About Rachel
I’m a builder first and an executive second. I am a seasoned product, engineering and design leader, founder and investor with over 20 years of experience. I have extensive experience with scaled P&L ownership, building scaled multiple AI native products, product-led and sales-led growth, multi-product innovation, and owning and driving results across the GTM functions.
My experience includes a diverse range of company stages (Seed - Series C, pre-IPO, public), multiple industries (SaaS, Consumer, Martech, Adtech, Service, Sales) and markets (US, EMEA, Asia-Pacific).
In the past, I have
- Built many AI workflow products over the last decade
- Owned a multi-billion dollar P&L
- Helped several companies go multi-product to stack S-Curves
- Build out product and engineering practices scaled to 1000+ employees
- Built several multi-million dollar product lines from scratch
- Recruited and managed stellar product & engineering organizations and leaders
- Raised capital at my own startup and supported raises at companies I work at
- Launched and managed enterprise SaaS products and 5-star Salesforce app
- Guided a product line to Gartner Visionary status
- Owned the product line for 2 different Comscore 100 media properties
- Become proficient in software engineering, data science and user experience
- Been recognized as a thought leader on customer data and product-led growth
- Given the keynote at several conferences and participated as a panel member at events
Specialties: product leadership, product management, multi-product, M&A, people management, product strategy, ux design, product marketing, new business development, competitive analysis, big data, analytics, AB testing, statistical analysis, behavioral experiments, business intelligence, talent management, performance management, social enterprise, viral flow, SaaS, enterprise software, mobile, advertising, monetization, applications, platforms, real-time, communication platforms, thought leadership, innovation management, entrepreneurship, launching start-ups, lean startup, ideation
Experience
- Chief Product OfficerDec 2023 - Present · 1 yr 9 mosCurrent
{}
- Angel Investor2021 - Present · 4 yrs 8 mosCurrent
{"0":{"type":"textComponent","text":"Invest in pre-seed, seed & series A across SaaS, AI, & Security. Bias for mission-driven founders."}}
University of California, Berkeley
- MentorJan 2021 - Present · 4 yrs 8 mosBerkeley, CA, United StatesCurrent
{"0":{"type":"textComponent","text":"Mentor at SkyDeck\nTeaching future product leaders in Product Management 186"}}
First Round Capital · Part-time
- Angel TrackOct 2021 - Dec 2021 · 3 mos
{"0":{"type":"textComponent","text":"Masterclass and community for angel investors. One of the 40 operators selected from 1300 applications for the 9th Angel Track Cohort."}}
- VP & GM, Dropbox Core & Gen AI Business Unit2020 - Jun 2023 · 3 yrs 6 mosSan Francisco, California, United States · Hybrid
{"0":{"type":"textComponent","text":"Reported to President and was a member of S-Team. Directly led product, engineering, growth, and AI and was accountable for a ~$2.5B P&L while serving over 800 million registered and 18 million paying users worldwide.\n\nLaunched first Gen AI product Dropbox Dash; led M&A of CommandE; drove Dropbox's AI transformation in search, automations, organization, and summarization using LLMs & ML.\n\nOwned P&L, roadmap, strategy, and operations for FSS (core product) across consumers, prosumers, self-serve, managed segments; Led team of ~550+ across Product, Engineering, Growth, including our AI / ML platform; located in US, EU, and Israel.\n\nLed multi-product strategy; launched new products in security (Backup, Passwords) and video (Capture, Replay) from idea to GA driving xxM WAUs growth; led M&A of DocSend ($165M acq) & Boxcryptor to grow our security TAM."},"1":{"type":"mediaComponent","text":"Dropbox to acquire secure document sharing startup DocSend for $165M","thumbnail":"https://media.licdn.com/dms/image/sync/v2/C5627AQH1s-TwYlXZFw/articleshare-shrink_800/articleshare-shrink_800/0/1712181562113?e=1756720800&v=beta&t=G9yNUr0wEaBGgbI98mfvfuF71dEp7L_CdIYXoW_cboo"},"2":{"type":"mediaComponent","text":"Welcome Command E to Dropbox!","thumbnail":"https://media.licdn.com/dms/image/sync/v2/D5627AQGV7vjnS9A5jg/articleshare-shrink_800/articleshare-shrink_800/0/1711924217546?e=1756720800&v=beta&t=YBOnF19XFch0Sama8s6DOV_hSAyko30upt9UuDXQ71E"},"3":{"type":"mediaComponent","text":"Dropbox acquires Boxcryptor assets to bring zero-knowledge encryption to file storage","thumbnail":"https://media.licdn.com/dms/image/sync/v2/D4E27AQHH7u2m9Ujkcw/articleshare-shrink_800/articleshare-shrink_800/0/1748983007540?e=1756720800&v=beta&t=T1JcbdWz5N8-pplpxOnhudskR2xIlHhuv7snX6gddq8"}}
- VP, Product & DesignJan 2019 - Sep 2020 · 1 yr 9 mosSan Francisco Bay Area
{"0":{"type":"textComponent","text":"Leading data connectivity platform for Fortune 500 companies to leverage customer data to drive organizational decisions and customer-centric experiences. LiveRamp has over 1400 employees globally and processes over 4 trillion customer records per month.\n\n• Owned global product roadmap that drove growth of P&L from $220MM to $380MM across a multi-product global portfolio of products including onboarding, integrations, measurement, analytics, data partnerships, international, and TV.\n• Led a global team of 40+ across Product and Design located in US, EU, and China.\n• Launched LiveRamp Safe Haven LOB, our customer data platform; drove significant Y1 revenue $xxm and xxx% growth in Y2.\n• Negotiated GCP & Snowflake channel deals driving $xxxm ARR in years 2 and beyond,\n• Co-led the acquisition of Data+Math, a TV Measurement company to solidify our position in the TV identity space; identified and championed DataFleets, a privacy technology platform to strengthen and future-proof our company and products."},"1":{"type":"mediaComponent","text":"LiveRamp Launches Safe Haven to Enable Data Partnerships","thumbnail":"undefinedundefined"}}
- VP, Product & Design2017 - 2019 · 2 yrsSan Francisco, CA
{"0":{"type":"textComponent","text":"Euclid was the world’s leading offline identity network. We served retailers, shopping malls and restaurants. Our investors included Benchmark Capital, NEA, Groupe Arnault (LVMH) and more. \n\n• Amazing ride 🚀acquired by WeWork,\n• Employed AI and ML to help our clients (JoAnn Fabric, Simon Property Group, A&W) build their customer data asset and predict customer behavior,\n• Drove pivot of product from spatial analytics to customer segment builder to real-time heat map that led to WeWork acquisition."}}
- Director (Head of), Product & Design2015 - 2017 · 2 yrsSan Francisco Bay Area
{"0":{"type":"textComponent","text":"Talkdesk is a cloud-based, enterprise-grade call center application and real-time communication platform using data science, machine learning, and artificial intelligence in the call center to predict customer behavior. I joined as the first Head of Product in the seed round when they were valued at $30m. Talkdesk is currently valued at $10B.\n\n• Owned portfolio of products including applications, services, integrations and platform; responsible for roadmaps, continuous deploys, bi-weekly releases across 14 development scrums (~70 developers),\n• Recruited and managed 17-person team across product, design, data; led teams in US and Portugal,\n• Launched two $MM+ new product lines in 2016 that opened new personas (Sales) and verticals (Healthcare),\n• Launched AI platform and recruited AI apps into our ecosystem,\n• Owned platform and applications that support a 99.999% (up from 99.99% when I joined) SLA with more than a 1000 customers, including many public companies,\n• Launched successful Salesforce app (4.65 stars, 696 reviews),\n• Started in-house data and design teams; evangelized design thinking and democratizing data intelligence throughout company,\n• Extracted learnings from data analytics and in-person user testing to drive key improvements such as our new Callbar application and platform,\n• Delivered keynote at Opentalk conference, \n• Evangelized product in sales and analyst meetings; pitched to Gartner, Forrester, etc.; helped secure nomination as Visionary in Gartner 2017 Call Center-as-a-Service (CCaaS) Magic Quadrant."},"1":{"type":"mediaComponent","text":"How to Build an AI Roadmap for Your Contact Center - Talkdesk","thumbnail":"https://media.licdn.com/dms/image/v2/D562DAQGCzijV4C8_BQ/profile-treasury-image-shrink_800_800/profile-treasury-image-shrink_800_800/0/1681750251718?e=1756720800&v=beta&t=GqOIrpe0QN7ZkOheodjblvfn5Y-GkpP-OgvuIaDt66k"},"2":{"type":"mediaComponent","text":"Opentalk 2016 - Product Keynote","thumbnail":"undefinedundefined"},"3":{"type":"mediaComponent","text":"Talkdesk Live | Teaser","thumbnail":"undefinedundefined"}}
- Co-Founder & CEO2013 - 2015 · 2 yrssan francisco bay area
{"0":{"type":"textComponent","text":"YadaZing helped English students learn real, conversational English from really entertaining videos. \n\n• Built a Natural Language Processing engine to automatically identify colloquial English phrases and educational web application\n• Sold content platform into Kaplan, Princeton Review and other private language schools\n• Recruited and managed 5-person team of product, engineering, and designers\n• Raised angel round; recruited top Silicon Valley investors and entrepreneurs as advisors"}}
- Senior Product Manager2010 - 2013 · 3 yrsSan Francisco Bay Area
{"0":{"type":"textComponent","text":"SAY is building the media company of the future to help independent publishers create compelling media and make a living through high-quality brand advertisement.\n\nI was the product team's Jill-of-all-trades.\n\n• Led product for site experience for ReadWrite.com, a Comscore 100 property; team's efforts grew search traffic by 4x\n• Led product for Typepad.com, a top 300 Comscore US site; led complete redesign of SaaS publishing platform\n• Led teams that built our publisher monetization analytics application; powered complex business workflows and drove insights for our publisher partners"}}
TimeBridge (acquired by Merchant Circle)
- Senior Product Manager2009 - 2010 · 1 yrSan Francisco Bay Area
{"0":{"type":"textComponent","text":"TimeBridge is a Mayfield-backed, online scheduling application for small businesses.\n\nI owned product functionality and drove new feature development. I conducted low-overhead, usability tests and implemented A/B testing of key features in the viral loop which increased user growth by 14% and user engagement by 4.3x."}}
- Business Development ManagerJun 2008 - Sep 2008 · 4 mosPalo Alto, California, United States · On-site
{}
Knightsbridge Solutions (acquired by Hewlett-Packard in 2007)
- Senior Software Development Engineer2004 - 2007 · 3 yrsChicago, IL
{"0":{"type":"textComponent","text":"Knightsbridge helped big customers wrangle big data. I was promoted three times and transitioned from an engineering to business role.\n\nI developed and deployed software (SQL, Perl) for large-scale ETL, data warehouse and business intelligence solutions for clients in our healthcare vertical (Kaiser Permanente, BlueCross Blue Shield). \n\nI also developed and helped implement the marketing strategy for external analyst relations which led to ranking in Gartner and our sale to HP."}}
Aha! Interactive (acquired by SchoolNet, now owned by Pearson)
- Software Development Engineer2003 - 2004 · 1 yrChicago, IL
{"0":{"type":"textComponent","text":"AHA! helped school districts improve teacher professional development. We serviced large districts such as Chicago Public Schools and New York Department of Education. I built and scaled the application platform (VB.NET) implemented for 15 U.S. K-12 districts. "}}
Education
- Northwestern UniversityBS, Computer Science, Organizational Change
- University of California, Berkeley, Haas School of BusinessMBA, Concentrations in Marketing, Entrepreneurship
Skills
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