Jonathan Hastings

Group Product Manager, Growth @ Squarespace

New York, NY


Office Hours

How does this work?

I’m a Group Product Manager on the Growth product team at Squarespace, working to help empower the independent workforce of makers, thinkers, and doers to stand out online. The PMs I manage focus on acquiring and activating new users across all of our platforms, including the end-to-end experience in the Squarespace native apps. Previously, I led the native mobile product teams at Rent the Runway, helping transform the way women get dressed and disrupting the $3 trillion fashion industry. My teams were responsible for finding ways to grow the emerging subscription business which quickly became the primary source of RTR’s revenue. Before that, I worked as product manager on Jet's catalog team for data optimization. I joined 3 months after its launch and stayed through the Walmart acquisition a year later. In my spare time, I serve on the Board of Trustees for The Foundation for Student Communication, a group founded at Princeton in 1968 by Steve Forbes to bring together undergraduate students and business leaders to equip the next generation with the tools and knowledge to solve the world's biggest problems. The Foundation is the publisher of Business Today magazine, the most widely distributed student-run publication in North America, and hosts a series of conferences inviting students and business leaders from around the world.

Ask me about
Product Management
Digital Strategy
Product Culture
Organization Development
A/B Testing
Product Hiring
Work experience

Feb 2020 - Present


Group Product Manager


May 2019 - Feb 2020


Senior Product Manager


Sep 2018 - 2020

Product School

Guest Lecturer


Oct 2017 - May 2019

Rent The Runway

Product Manager, iOS & Mobile

• Managing roadmap, strategy, and execution for native mobile and mobile web; agile iOS team includes 8 front-end developers (Swift), 1 back-end developer (Java and Python), 2 QA Analysts, 1 Product Analyst, and 1 UX/UI designer • Within three months at RTR, also began leading product initiatives for subscription growth to expose subscription options at different points in funnel with an additional agile team: led a series of A/B tests resulting in greater than 75% growth in subscription sign-ups, scaled to 13% revenue growth in total eCommerce business and 32% increase in MRR • Creating unique, "mobile-first" experiences to improve conversion, new order growth, and customer loyalty in RTR's highest-performing channel by better leveraging customer data for personalization and recommendations, recognized as Apple’s App Store App of the Day twice since I joined • Building strategy and technical implementation plan for online display ads and paid social campaigns for the first time in the company's history

Dec 2016 - Sep 2017

Associate Product Manager

• Product owner and responsible for roadmap for most widely-used internal tool across Jet and Walmart-eCommerce used by Catalog Operations, Pricing, Product, Member Services (Customer Service), and Retail Teams • Leveraged a combination of qualitative and quantitative data such as user feedback sessions, Azure Insights, Adobe Omniture, and Sales (SQL) to build a strategic roadmap for greatest business impact in GMV and conversion, and to reduce friction in user experience • Led product front-end and back-end design process including user workflows and UX/UI design, JavaScript development framework decisions, and building and iterating on an entirely new RESTful API • Brokered consensus among diverse set of cross-functional stakeholders to prioritize features for business needs • Scoped and implemented manual workflows and UI for hourly, outsourced, and crowdsourced users to improve catalog data quality and train semi-supervised machine learning algorithm

Dec 2015 - Dec 2016

Sr. Analyst, Jet Direct

• Core member of  “strategic-category” working group, reporting directly to CRO and CEO to identify levers for increasing GMV, boosting margin, reducing churn, and improving on-site experience; prepared actionable plan to scale across retail for best practices • Analyzed sales, basket, and transaction data in SQL to identify Key Value Items in category to drive new pricing strategy, resulting in approx. 14% lift in GMV and 36% improvement in (simple) margin • Identified consumer decision tree in category through analysis of Adobe Omniture click-through data on site elements and executed plan to improve conversion and reduce bounce and churn


Dec 2013 - Jan 2015

Business Today


Started by Steve Forbes in 1968, Business Today brings together undergraduate students from around the world and business leaders to empower the next generation to solve problems and create better outcomes. • Led the organization in its 46th year of operation; managed $1,100,000+ P/L and oversaw $2,000,000+ AUM endowment • Radically exceeded revenue goals, with 2.5x increase in YoY revenue and 2x increase in conversion • Managed relationships with 250+ c-suite corporate contacts and partners, including majority of Fortune 100 with partners such as CEO of Coca-Cola, Global MD of McKinsey & Co., and CEO of New York Times • Expanded “Startup Conference” co-hosted with Sequoia Capital to largest selective undergraduate-run startup conference in the country

Jun 2014 - Aug 2014

Parkman Whaling

Summer Analyst

• Assembled management presentations, pitch books, and other marketing materials for prospective clients • Performed valuations using public comps, precedent transaction and DCF analyses • Modeled cash flow from oil and gas well-economics and estimated decline curves


Mar 2013 - Nov 2013

Business Today


Jun 2012 - Dec 2012

ESS Funds

Intern (Private Equity)

Apr 2011 - Aug 2011

Swift Energy Company

Investor Relations Intern


2011 - 2015

Princeton University

A.B., Public Policy & International Affairs

Trade & Finance Policy Cluster; Senior Thesis: Labor Participation Implications for Corporate Bankruptcy Policy in Argentina

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