Shopify · Go-to-market · Senior · 45 to 60 minutes

Should Shopify Move Upmarket Now?

Shopify is a commerce platform that helps merchants build, run, and grow online retail businesses. Answer this product management case and get it graded line by line against a weighted rubric.

Strategic thinking
Go-to-market
Segmentation
Executive communication
Tradeoff analysis

The situation

You are a senior PM at Shopify, working with the CRO and product leadership in late 2022. Shopify is strong with entrepreneurs and SMBs, but some larger merchants are showing interest in the platform as commerce teams rethink cost, speed, and platform flexibility. At the same time, many enterprise brands still use more complex and expensive systems, and switching platforms is risky. Leadership wants a recommendation on whether Shopify should make a focused push into enterprise now, and if so, how to take it to market without hurting the core business. The decision is hard for three reasons. First, enterprise buyers have different needs, including reliability, support, release control, and procurement expectations. Second, Shopify’s brand and product are strongly associated with simplicity and fast merchant self serve adoption, so an enterprise motion could add complexity and internal distraction. Third, if Shopify waits too long, it may miss a market window as larger merchants look for faster implementation and lower total cost of ownership. Assume Shopify can fund a meaningful but not unlimited investment over the next 12 to 18 months.

What to produce

Write a 2 to 3 page go-to-market recommendation memo for Shopify leadership.

Your answer must

State whether Shopify should enter enterprise now, later, or not at all, and define the specific customer segment you would target first.
Explain the market timing and buyer pain points, including why larger merchants might reconsider their commerce platform now.
Propose the go-to-market approach across product packaging, positioning, sales motion, and proof points, with a clear view on total cost of ownership.
Identify the minimum enterprise specific capabilities or service changes required to make the offer credible, and what should remain unchanged in the core product.
Lay out a phased 12 to 18 month plan with success metrics, major risks, and how you would prevent harm to Shopify’s SMB business and product simplicity.

Constraints

Do not assume a full rewrite of Shopify’s platform.
Do not rely on cutting price alone as the main strategy.
You must preserve Shopify’s mission and strengths in speed, usability, and broad merchant appeal.
Your plan should work even if enterprise sales cycles are materially longer than SMB sales cycles.

Format

Use sections for recommendation, why now, target segment, go-to-market plan, product and service implications, metrics, and risks.

How Shopify actually played it

Follow-up on how Shopify moves into enterprise, with an interview on selling to larger merchants.

Moving upmarket changes product and sales
Learn from those running the motion
Platforms must serve different customer sizes

Built from How Shopify Grows: Part 2 by Jaryd Hermann (How They Grow).