Core Strategy Senior Lead

About the company the company is a technology wholesale platform built on the belief that the future is local. Independent retailers around the globe collectively represent a multi-hundred-billion-dollar wholesale market that has historically been fragmented and offline. At the company, we're using the power of tech, data, and machine learning to connect this thriving community of entrepreneurs across the globe. Picture your favorite boutique in town — we help them discover the best products from around the world to sell in their stores. With the right tools and insights, we believe that we can level the playing field so businesses can grow and local communities can thrive. We’re looking for smart, resourceful and passionate people to join us as we power the shop local movement. If you believe in community, come join ours. About this role The Core Strategy team reports directly to our CEO and is tasked with solving some of the company’s most urgent and challenging problems. This can range from driving investment decisions on major expansion opportunities to directly owning pilot execution on high potential new bets. We operate at a wide range of altitudes and across all areas of the business. You will be joining a small team with a high degree of autonomy and responsibility. The work will vary project-to-project, but the throughline is that you will be taking ambiguous, complex problems, creating clarity, and then driving to impact. In many cases that will mean you are directly owning outcomes for high priority pilots or other initiatives. As an example, our team drove the decision to launch the company Source and then played a central role in building the program from the ground up alongside a small cross‑functional team. This role combines strategic thinking, analytical rigor, product judgment, external & internal relationship‑building, and the operational chops to get things done. We are looking for someone who is equally at home unpacking ambiguous board‑level strategy questions as they are running a scrappy pilot. No matter the project, success in this role will always look like creating clarity and then seeing that clarity through to real‑world impact. What you’ll do Take ambiguous, high‑stakes problems from first framing through to implementation Break down complex questions from first principles, with a mix of analytical rigor, customer insight, and collaboration with internal and external experts Consistently raise the bar on how our team uses AI to get to better answers, faster Collaborate closely with the product, analytics, marketing, finance, and ops teams to solve problems and drive through execution to outcomes Spot cross‑functional dependencies early and unblock them yourself Present your recommendations and debate their implications with the company’s executive team, guiding key company decisions Help shape the culture and capabilities of the Core Strategy team by improving our processes, mentoring teammates, and setting a high bar for excellence Qualifications A Bachelor’s degree and 8+ years of experience across consulting, business operations, product, strategy, or analytics roles Exceptional problem solving skills and ability to identify and synthesize insights from data Deep analytical toolkit, with strong proficiency in Excel, SQL, and AI tools Executive‑level communication skills, including the ability to use verbal and written communication to express ideas clearly and succinctly Excellent at breaking down unstructured problems and synthesizing many disparate sources of information to deliver simple and thoughtful answers Strong business judgment, with ability to think across every dimension of the business Experience with quantitative and qualitative consumer and market research techniques Ability to operate with a high degree of autonomy and ownership Curiosity, low ego, and willingness to learn from a wide range of people Salary Range San Francisco or New York City: the pay range for this role is $197,500 - $271,500 per year. This role will also be eligible for equity and benefits. Actual base pay will be determined based on permissible factors such as transferable skills, work experience, market demands, and primary work location. The base pay range provided is subject to change and may be modified in the future. **Hybrid the company employees currently go into the office 3 days per week on Tuesdays, Thursdays, and a third flex day of their choosing (Monday, Wednesday, or Friday).* Additionally, hybrid in‑office roles will have the flexibility to work remotely up to 4 weeks per year. Specific Workplace and Information Technology positions may require onsite attendance 5 days per week as will be indicated in the job posting.* Why you’ll love working at the company Move fast: You'll own meaningful problems that serve customers around the globe with the agency to move fast and see your results clearly. Equipped to scale: We invest in what matters, including the latest enterprise AI tools, to help you work smarter and get more out of every day. Best in class: Our team is full of sharp, kind, and generous colleagues who care about their craft and about helping you grow in yours. Real rewards. Competitive pay, equity, and comprehensive benefits designed to support your life inside and outside of work. Belonging: We're intentional about building an environment where every the company employee has equal access to opportunities, growth, and success. the company was founded in 2017 by a team of early product and engineering leads from Square. We’re backed by some of the top investors in retail and tech including: Y Combinator, Lightspeed Venture Partners, Forerunner Ventures, Khosla Ventures, Sequoia Capital, Founders Fund, and DST Global. We have headquarters in San Francisco and Kitchener‑Waterloo, and a global employee presence across offices in Toronto, London, and New York. To learn more about the company and our customers, you can read more on our blog. the company provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity or gender expression. the company is committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. Accommodations are available throughout the recruitment process and applicants with a disability may request to be accommodated throughout the recruitment process. We will work with all applicants to accommodate their individual accessibility needs. To request reasonable accommodation, please fill out our Accommodation Request Form ( company-form) Privacy For information about the type of personal data the company collects from applicants, as well as your choices regarding the data collected about you, please visit the company’s #J-18808-Ljbffr United States Digital Space LLC