10th Anniversary NY Enterprise Tech Meetup: How the CEO of Attentive Navigated a Massive Pivot to Find Product Market Fit

Mar 1, 2022
10th Anniversary NY Enterprise Tech Meetup: How the CEO of Attentive Navigated a Massive Pivot to Find Product Market Fit
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This month, we celebrated the 10th Anniversary of our NY Enterprise Tech Meetup! To honor our New York roots, we welcomed Brian Long, CEO and Co-Founder of one of NYC’s most exciting giants, Attentive, to our Zoom stage. Valued at over $2.2B, Attentive is a comprehensive mobile messaging platform for over 4,000 brands, such as Urban Outfitters, Michaels, Coach, and more.

As one of the most practical conversations we’ve had to-date, Brian dove into what Attentive’s product-market-fit journey was like in the earliest days (spoiler alert: there was a BIG pivot involved) and the tactics he used to position the company for mega-growth. See our recap of Brian’s insights below and watch the full webinar recording here.

There Are 3 Types of Software Founders Can Build Today

  1. Software that makes money for customers
  2. Software that saves money for customers
  3. Software that does neither

In terms of finding true product market fit, bucket #1 is the easiest. If you’re able to drive more revenue for a customer, it’s an easy sell as every company wants to make more money. Admittedly, this is the bucket Attentive always strived to be in as they navigated product market fit and built out their platform.

The 🔑 to Product Market Fit: Researching & Understanding the Customer Pain Point

For any of the three buckets above (especially the more challenging sells of #2 and #3), researching and understanding the customer pain point should be the top priority in the early days. According to Brian, “taking time to talk to customers will never be a waste of time,” comes with almost no downside, and is critical in defining your product roadmap.

Tactic: Find people who are comfortable giving you direct and honest feedback. When you source product feedback from friends or family, a lot of them will tend to give the polite response of “that’s cool.” While it may feel good to get a positive response, in reality, these fluffy responses will yield no help in building a more viable product. Instead, source feedback from customers or other third party groups that are more likely to give a critical review.

Tactic: Break down your sales deck into four clear sections — a two minute elevator pitch, the problem, your solution, next steps. When talking through the problem, the goal is to determine if that problem is actually high on the customer’s list of pain points and then if your solution would adequately solve that problem for them.

Tactic: Give customers specific metrics to report to determine the feasibility of the problem and solution. Asking customers open-ended questions such as “Would this help you or how much would you pay for this?” won’t result in concrete responses. Instead, ask them to report real numerical values. Early on, Brian established a NPS-like scoring system where customers could rate the product from 1 to 10 (1 being “I would never buy this, this is not a problem” and 10 being “I need to buy this now, this is our #1 pain point”). On this scale, 1–7 was not good, 8 was ok, but the 9s and 10s signaled real product market fit.

What this looked like at Attentive: Thanks to this mission critical customer feedback, Brian and his early team realized they needed to scrap everything only 7–8 months into building the business. Originally, they set out to build a company called Franklin, a mobile messaging platform that communicated with distributed workforces. After pitching 150+ customers and analyzing their feedback, the team realized the platform wouldn’t be a high growth business, and that executives were willing to spend a lot more money to communicate with customers vs. workforces. So they pivoted. They re-launched with a new name (Attentive), new product, new strategy and even fired a few people. From there, Attentive’s new product was able to garner early customer feedback in the 9s and 10s. While some investors were wary of the pivot, ultimately this was a life-saving move for the company. Even though finding product market fit in under a year is pretty fast compared to industry standards, Brian admits he regrets not pivoting earlier on.

Sell Early, Often & Aggressively

A lot of startups exist without a sales team up until their Series A fundraise. Without a sales team, your ability to communicate and win prospective customers at any scale suffers. While Brian believes there’s no one-size-fits-all sales hiring strategy and that you need to do what’s right for the DNA of the founding team, he warns founders not to stack up their early team with only engineers and product people. These teams can build, but they can’t sell.

Tactic: Hire two or three SDRs in the early days. This squad will help get the ball rolling faster on booking meetings and increasing customers in the funnel. Not to mention, this is cheaper than hiring more engineers. Once you’ve surpassed momentum the SDR team can handle, then hire a senior salesperson.

What this looked like at Attentive: Attentive had four SDRs from the very get-go. Once Brian knew they were on the right track in terms of their product market fit, he hired a VP of Sales. No matter what stage your company is, you need someone to be the external voice of the company’s go-to-market strategy. While it’s rare to hire an early VP of Sales who stays with the company through years of growth, Attentive’s VP of Sales is still there as their CRO.

Bonus: Brian’s Top Book Picks

If you’d like to stay in the loop on all upcoming Work-Bench NY Enterprise Tech Meetups, drop your email below 👇