Empowering teams to drive business impact while making progressive decisions along the way.
Hi, I'm Mary!

I have almost a decade of experience leading projects and designing applications for web, iOS, and Android across many different industries including sports tech, real estate, e-commerce, enterprise software, and more. I help companies define, design, and launch world-class digital products from 0-1 by aligning teams, stakeholders, and customer expectations.

I’m currently a Senior Product Design Manager at Underdog, where I’m focused on building and scaling the design organization. Before this, I led the design for Eventbrite’s ad product, driving a +525% revenue growth in just 12 months. Prior to that, I served as the Head of Product Design at SuperDraft, a sports tech startup, where I designed two highly successful products—Fantasy and Sportsbook—now serving over 200,000 users and generating more than $50M in revenue.

As a Startup Design & Growth Partner, I specialize in helping startups scale by leveraging my expertise in design strategy and user experience. I work with startups in various stages of growth, from seed to series A and beyond, and am committed to building long-term relationships with founders and teams. Over the past few years, I have helped secure over $560M in investments in partnership with my designs. By understanding unique challenges, I develop custom solutions that meet their needs, whether it's developing a winning product strategy, optimizing user experience, or driving growth.
Core values behaviors
Seeing every day as an opportunity to turn values into action.
Earn customer trust
Building trust with clients and users through transparent communication, timely delivery, and a commitment to meeting their needs.
Get it done, do it right
Balancing speed and quality to deliver products that meet the needs of the business and exceed expectations.
Practice candor with care
Communicating openly and honestly, while being sensitive to needs and concerns.
Dream big, ship often
Encouraging bold thinking and rapid iteration, with a focus on moving quickly and delivering value.

Experience

Senior Product Design Manager, Underdog

Oct 2024 - Present

Currently scaling the design team and our operations while driving business growth through strategic design initiatives.

Product Design Manager, Eventbrite

Dec 2022 - Aug 2024

Lead the product and design vision for Eventbrite's new ad product while building systems to improve design operations.

  • Led and developed a lean, high-performing, design team across three engineering squads, fostering a culture of innovation and accelerating professional growth
  • Initiated the definition of objectives, high-level strategies, and key outcomes for the design team, driving towards impactful contributions
  • Crafted and executed strategic design vision that guides cross-functional leadership in shaping the pillar’s direction, presenting ideas to the executive team to secure buy-in
  • Redesigned Eventbrite's ad creation flow, resulting in a 72% increase in conversion rate (18.6% to 32%) and contributing to a 224% revenue surge within six months
  • Spearheaded initiatives that boosted monthly active advertisers by 533% and revenue by 525%, including a complete overhaul of marketing tools entry points and the ads insights dashboard

Senior Product Designer, Eventbrite

July 2022 - Dec 2022 • 6 mos

Defined product strategy for the creator navigation team leading two cross-team initiatives.

  • Guided and mentored fellow product designers, fostering skill development and knowledge sharing within the team
  • Conceptualized and crafted an innovative dashboard for the Creator segment of Eventbrite's marketplace, enhancing user experience and facilitating streamlined navigation
  • Played a pivotal role in shaping the design culture by initiating and
    conducting regular design critique sessions, elevating the quality of design output and fostering an environment of constructive feedback and growth
  • Contributed to the strategic planning for 2023 across not only the direct team but also two additional teams, ensuring alignment with company goals

Head of Product Design, SuperDraft

Aug 2021 - July 2022 • 1 yr

Cultivate a conducive environment for great design while overseeing all product design initiatives for SuperDraft’s five core products.

  • Scaled the design organization from 1 to 8 members, overseeing product, content, brand, and product marketing, while managing two supporting design agencies
  • Key contributor to securing $10M in funding, leading the creation of pitch decks and materials, and co-presenting to potential investors with the executive team
  • Contributed to achieving $50M in revenue by supporting the expansion of the user base to 200k over a three-year period
  • Established and executed strategic objectives, high-level strategies, and key results for the design team, directly reporting to the CEO
  • Developed a comprehensive design system in Figma, unifying the visual and functional design across four products (Fantasy Sports, Sports Betting, iGaming, NFT) on both web and native platforms
  • Led the design and strategy for three innovative game modes, driving them from concept to launch in just two months, resulting in a 245% increase in entry fees
  • Created a new mobile onboarding experience based on user data, leading to a 516% increase in deposit rates

Product Design Manager, SuperDraft

Jan 2020 - Aug 2021 • 1yr 8mos

Established growth strategy and process for product design while continuing to be a key contributor to product deliverables.

  • Built and refined the recruiting pipeline process, successfully hiring and onboarding for every department, expanding the team from 4 to 60+
  • Contributed to strategic decisions in collaboration with the executive team while managing the product roadmap
  • Implemented daily standups, weekly 1-on-1s, and monthly design retrospectives to mentor and empower designers
  • Refined the design process and cross-team communication by creating a greenlight process, structuring stakeholder review meetings, and building handoff templates
  • Applied Agile methodologies to promote a disciplined and transparent process across teams, while overseeing product owners and quality assurance teams

Lead Product Designer, SuperDraft

Mar 2018 - Jan 2020 • 1 yr 11 mos

Spearheaded the launch of two major products—Fantasy and Sportsbook—from 0 to 1, serving as the sole product designer and directly reporting to the CTO.

  • Developed and executed a comprehensive beta research plan for SuperDraft’s core Fantasy product, including user interviews, surveys, and data analysis to inform product development
  • Directed all product design initiatives, creative direction, and communication strategies, ensuring alignment with business objectives
  • Collaborated across departments to create internal presentations, pitch decks, and infographics, prioritizing and achieving business goals with timely execution
  • Conceptualized, designed, and managed Facebook Ad campaigns, driving user engagement and acquisition
  • Hired and managed two external design agencies, leading the creation of 200+ marketing assets for digital advertising campaigns

Designer, Society Nine

Sep 2017 - Aug 2018 • 1 yr

Supporting the Founder with user experience guidance and design direction for their products and website.

  • Conducted user testing and generative research to identify and implement key website improvements
  • Designed branding elements, including infographics, logos, and apparel, ensuring consistency with visual and textual standards
  • Designed infographics and logos explaining new product lines meeting visual and textual branding standards
  • Supported design work on training gear packs and apparel

UX/UI Designer, 36creative

Jan 2018 - Mar 2018 • 3 mos

First in-house UX/UI designer creating design process and advocating for user research.

  • Led the initial stages of client engagement, from delivering compelling company pitches to crafting tailored proposals
  • Presented design solutions that effectively balanced user expectations with business goals, securing ongoing client partnerships
  • Gathered and analyzed data from user testing and interviews to create detailed user personas, journey maps, site maps, wireframes, and prototypes

Recent Freelance

Lead Product Designer, Yureka

Product Comparison Tool (B2B, Saas)

Designed product from zero to one including core flows, prototypes, and user research.

Lead Product Designer, Better

Digital-First Homeownership Platform (B2C)

Designed multiple new landing pages, conversion funnels, and dashboards for Better's mortgage and insurance products.

Lead Product Designer, Generation Esports

E-Sport Leagues for Educational Institutions (SaaS)

Defined strategy for new a new web platform and designed onboarding flows to optimize conversion.

Lead Product Designer, Bartesian

Premium Cocktail Machine (Ecommerce)

Focused on e-commerce optimization through landing page redeisgn and product strategy for the checkout funnel.

Lead Product Designer, HireRoad

Employee Onboarding Software (SaaS)

Collaborated with the CPO to create a total redesign of their software based on their redesigned brand and design system.

Senior Product Designer, Astec Industries

Equipment Management IoT/Cloud Platform (SaaS)

Supported design work for Astec's new platform, including dashboards, widget customization, and data visualization.

Education

B.S. Industrial Design

Wentworth Institute of Technology, 2017

Edward T. Kirkpatrick Cooperative Education Award
Chi Alpha Sigma National College Athlete Honor Society (Soccer)

Foundations of Creative Leadership

IDEO U, November 2024 (Expected)

Courses: Leading for Creativity, Storytelling for Influence, Cultivating Creative Collaboration

Endorsements from people I have collaborated closely with.

Lauren Nagra
Senior Product Manager

"Mary is a force on the design team. She ties every decision back to the customer problem, is incredibly data-driven, has great product intuition, and constantly takes ownership/shows initiative to make our product and processes better."

Rosie Steinberg
Senior Data Analyst

"Mary is a shining star. She is fun to work with, a diligent team member, and a clear communicator. She consistently stretches beyond the scope of design to provide thoughtful and insightful product and analytics feedback."

Tyler Davis
Senior Marketing Manager

"If you're looking for an insightful, thoughtful designer with an incredible talent for designing digital products, you couldn't ask for a better person to work with than Mary."

Andy Magnes
VP of Marketing

“Mary’s talent and professionalism significantly exceeds her experience and would be a tremendous addition to any product team. Supremely talented.

Alex Andrews
Senior Product Owner

“Mary is a one-of-a-kind Design leader with a great deal of knowledge, who empowers her team with freedom in their work and above all else, has the ability to grow a team and set them up for success.”

Andrew Wang
Junior Software Engineer (Web)

"Collaboration with Mary on bringing her UI designs to fruition is an experience I can only hope to match at future jobs. The consideration and polish she puts into her work, along with the passion and purpose she brings to each meeting, can truly invigorate an entire team."

Mary Annon

Product Design Leader

Let's Talk.

marygraceannon@gmail.com
603 545 8961