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Building an Enterprise-Ready Product

Solving the "User vs. Chooser" Dilemma

Last month, Salesforce officially closed on its record-breaking $27B acquisition of Slack. This closing is monumental for a variety of reasons. (Check out my partner Jake’s thoughts on how this move signals the evolution towards Deep Collaboration.) My personal favorite is that it marked the melding of two companies with completely opposite approaches to building out early product. Salesforce was, and continues to be, the quintessential poster child for SaaS businesses with a top-down, outbound selling motion and a buyer-focused product to match.

Meanwhile, Stewart Butterfield, CEO of Slack, was infamously quoted in 2016 at SXSW saying that he is not interested in hiring salespeople to help sell his product to companies, confident that his product’s user love and virality would single-handedly continue to drive their growth.

Fast forward to today, and Slack has a Sales team of over 500 people. To go from no Sales team to a 500+ person organization required more than just hiring great salespeople. It also meant re-thinking the way the product organization was structured, and how the team prioritized the way they built product.

During conversations with founders, we find that many early-stage founders grapple with the balance between building out products for end-users vs. the enterprise buyer. We call this dilemma the “user vs. chooser” problem.

We were lucky to discuss this topic with two early product leaders at Slack: Ilan Frank, VP of Enterprise Product, and Paul Rosania, former Sr. Director of Product. Below, we captured a few of the questions and answers that we found most helpful from the conversation.

1. When should I hire my first enterprise-focused product manager? 

When building product, focus on the end-user first. 

Do not hire an enterprise product lead for as long as you can hold out. Some may need to do this sooner than others, but in the early days it is critical that your end users love your product vs. building features for your buyer (chooser). 

While exact timing may be different from company to company, the #1 priority in the early stages is end-user happiness. Focus you and your team’s efforts on building the best end-user experience possible early. 

2. What role does the end-user play in the purchasing decision?

When moving into an enterprise purchase, it is important to bring the end-users into the conversations. Focus on your die-hard product advocates, and have them champion the purchase when engaging in enterprise-buying discussions. 

The best way to do this? Think about how you can make the user a hero within the organization. If you provide some type of magic in their day or make their life easier, then you have found the truest form of product activation. 

Finding this true activation event will speak much louder than any A/B test or data captured in the early days of building product. 

3. How do I balance between serving several enterprise logos and the smaller retail side of the business?

A successful strategy for gaining traction in the enterprise is to not overgrow the product when pulled into enterprise conversations. Think: crawl, walk, run.

When working with enterprises, first focus on individuals and small teams. After nailing those segments, you can then start building towards departmental use cases. Finally, once there’s enough pull from a handful of your largest customers, you can then start to build features and functionality required for enterprise-wide deployments.

Warning: It is important to manage expectations effectively when working with early enterprise customers. It will be difficult to say no to a large potential customer, but saying yes oftentimes will require too much of your team’s bandwidth, and will hinder your teams’ ability to deliver on core product features. 

Remember, no doesn’t necessarily mean no, it just means not now!

4. How should early-stage teams balance ad-hoc requests from prospective enterprise customers? 

We also frequently get asked, “How should teams decide between what to build and what to put on the back burner?

Structure your enterprise roadmap as a series of TAM unlocks. View certifications and certain functionality as a means to unlock different TAM opportunities within your customer base. Use this as a framework to drive decision-making on what is important to build now vs. later. Always anchor towards what features will be extensible to the majority of your other customers in your near-term future.

Pro-tip: If you haven't already, start a Customer Advisory Board (CAB) as soon as possible. A CAB is different from user/customer research. Instead, leverage the CAB as a way to learn more about customer deployments and how to make them most successful. (E.g., What is blocking deployment? What is blocking growth?) 

The recommended persona to invite into your CAB is the lowest-level admin at your customer that you can find. This person is typically responsible for product success, but gets their hands dirty in the day-to-day management of your product at their company. These people will know what’s holding back expansion, what features are required by security/compliance, and will be able to point to specific use cases where your product is seeing success. 

Keep in mind that CAB's are most successful when the group is small enough for a room (or to fit on one Zoom screen) in order to keep all participants actively engaged in the conversations. 

For more detail on CABs, check out 7 Tips to Run An Effective Customer Advisory Board from Gainsight.


We hope these answers help as a framework for some of the core decisions you and your team are actively thinking through. 

Is there a topic that we can delve into deeper? Any other topics we should cover? Drop me a note at or comment on our LinkedIn post.

Special thanks to Ilan Frank and Paul Rosania for contributing their expert insights.