Justin Grant

Hi! I'm a B2B product manager for Bay Area startups. That means I help people enjoy work by replacing paper, email, Excel, and/or someone else's crappy software with mobile & web tech that automates boring stuff, simplifies hard stuff, and makes impossible stuff possible. I make power tools for minds.

I'm looking for a startup to join! Ideally an early-stage one with a product-focused CEO who’s ready to delegate some Product work in order to better focus on CEO-ing. I did this at Cantaloupe Systems where I led PM from early-stage to $16M ARR and a 4x-to-investors exit. I'd like to do that again!

I'm focusing my search on what I know best: developer tools/APIs (the next Algolia or Vercel) or tech that manages physical stuff (the next Flexport or PlanGrid).

• Sabbatical + Open-Source Work + Blogging

  After my startup failed, I wanted to take time off to recharge. At least that was the dream. In practice, I've been mostly heads-down on two nerdy side projects while I figure out what's next:

  • Designing Temporal, the new date/time API for JavaScript. I started by giving the team feedback on the API, was invited to join to help lead its design, and ended up working on it almost full-time for a year. It's on track to ship in browsers and Node.js in 2022. 🚀
  • Writing my SaasPM blog on Substack, focusing on what I've learned doing Product in B2B startups. I've written about competitive strategy, working with a product-obsessed CEO, technical debt, gaining respect from engineering teams, managing feature requests, release communication, PM interviewing, and more.

• My Startup That Was Killed by COVID

  It’s been my long-term dream to take the hassle out of scheduling time to see friends in person. Like Uber for your time, or Tinder for existing friends. After Cantaloupe’s exit, I took a year to design and build a basic in-person social network where you add your friends, periodically record your free time (usually in response to notifications), and the app tries to match friends who want to hang out at the same times. That's the easy part. The hard part is managing the complex social dynamics that come with in-person plans. For example, how to avoid hurting feelings of a friend who you don't want to see more than 1x per year? How to avoid looking like a loser who's always free? How to avoid only hanging out with losers who are always free? How to be able to cancel if you're tired, without encouraging flakes? And so on.

  I bootstrapped a product from nothing to something. Designed UX workflows. Defined tech stack. Improved my (very!) rusty engineering skills. Built MVP (minimum viable product) on a glidepath to alpha release for early adopters in March 2020. Can you spot the flaw in this plan?

  

  2020-21 was obviously incompatible with a new in-person social network, especially one focused on strengthening an extended network of “weak-tie” connections. Before COVID hit, I was already close to my limit of motivational (and financial!) patience. Waiting yet another year (or more!) to know if the idea was going to work was just too much. So I opted not to make my MVP into a business. Instead, I'm going back to what I’m best at: SaaS Product Management!

• Cantaloupe Systems

  From 2011-2018 I led PM at Cantaloupe Systems, the leading SaaS provider for the $10B+ worldwide vending industry. After an $85M, 4x-to-investors acquisition by USA Technologies (later renamed to Cantaloupe, Inc.), I led PM for the combined company for a while before leaving to take time off to work on some nerdy side projects and to start something new. Here's what we did at Cantaloupe:
  • Enabled cashless (card swipes or mobile tap) payments at vending machines, growing our cashless product to #2 in the industry behind our eventual acquirer
  • Tracked near-real-time machine inventory and used that data to generate "prekits" to save warehouse and driver time
  • Managed one of the largest B2B IoT networks in the world, with 100,000s of cellular-modem-connected vending machines
  • Automatically built daily route schedules to optimize driver time and reduce vehicle and fuel costs
  • Algorithmically adjusted machine planograms to increase same-store sales and reduce "empties"
  • Managed warehouse operations and handled back-office accountability for cash and merchandise
  • Built mobile apps for very low-tech route drivers and warehouse workers
  • Built an ERP/CRM system for the vending industry, optimized around vending-specific workflows and analytics

• Splunk

  From 2009-2011 I did PM at Splunk, a big-data software company in San Francisco. I was responsible for Splunkbase app marketplace and Splunk Answers support community. I also drove Splunk's overall product-to-Web strategy: ensuring our app store and other community sites were seamlessly integrated into product features, were relevant for business users (not just online-community enthusiasts), and easy to use from inside the product.
  
  I also led the team that built Splunk's Application Management solution, managing the cross-functional team that delivered V1.0, which focused on analytics, operational reporting, and troubleshooting for Java Application Servers.

• MSDN and TechNet

  I was PM of msdn.com and technet.com, which at the time were the Web's largest community sites for developers and IT-Pros. I built out an analytics team (and the tech behind it), defined customer-success metrics and helped the team improve them, integrated MSDN with Visual Studio, grew Microsoft's online developer communities, and built an "internal SaaS" model to lower editorial and globalization costs. I also overhauled site navigation across 10M+ pages and improved site search.

• Microsoft Server Management Products

  I co-founded the team that built Microsoft's first Application Management product, leading a team that grew to 20 PMs responsible for Microsoft's server-management products including Operations Manager (now called SCOM).

• Stockpoint

  I was employee #7 of Stockpoint, a web-based financial information provider. I led web development, managed site operations, and scaled out Stockpoint's SaaS offering. Stockpoint was acquired and is now Dow Jones Client Solutions, part of News Corp.

• Ask Jeeves

  A part-time college job turned into me being employee #3 at the company that became ask.com. I split my time between pay-the-bills consulting projects and the early AskJeeves.com site. I remember the day our CEO brought the original "butler" art back from the graphic designer. At the time, I thought: "A butler? That's dumb. No one will use that!". ;-)

• Before I started writing my blog at SaasPM.com, I had fun writing longform answers to PM questions on Quora. You can get a good sense of how I approach PM from these answers. For example:

  What is PM?

  • What does the VP of product do when there is a product focused CEO?
  • Why does the role of a product manager vary so much from company to company?
  • Should the product manager be a generalist or a subject-matter expert?
  • What are some non-obvious responsibilities of product managers?
  • Why do companies need both product managers and product owners?
  • What are some advantages and disadvantages for a software engineer to become a product manager?
  • What are the pros and cons of working at a startup as a product manager versus at a large company?
  • In a SaaS company, who does the senior product exec typically report to?
  • As a software product manager, how is ambiguity bad, but being scrappy is good? What's the difference between the two?

  Product Strategy

  • What’s the biggest mistake you’ve ever made as a product manager, and what did you learn from it?
  • Is it possible to compete with bundled SaaS products when your products solve only one particular problem?
  • Why would a Product Manager ever entertain feature requests from low paying or freemium customers if that feature does not benefit the high paying customers?
  • What are the ways to go about, and things to consider when naming a product?

  Planning, Roadmaps, and Communication

  • How does an enterprise SaaS product avoid feature creep when most product decisions are support tickets-driven, as you are expected to always listen to your customers?
  • Ideally, how much of a Product Manager's time should be spent supporting sales requests for new features in order to close deals?
  • As product managers, do you periodically send an internal email to the company about what the product team is up to/has accomplished?
  • Do you ship your product even if you are embarrassed about it?
  • What do product managers typically discuss in their customer account review with upper management?
  • How do vertical SaaS companies get valuable customer feedback given that all their customers are competing with each other?
  • Do SaaS solutions release product roadmaps?
  • What's the best and easiest way to classify user verbatims from a survey?

  Collaborating with Engineers

  • As a Product Manager, how do you demonstrate value to your team?
  • Should a product manager be involved in technical architectural design?
  • Is it harder to go from software engineering to product management or the other way around?
  • Who determines how to spend software engineering time?
  • Is it dangerous for product managers to focus on technical debt?

  Mentoring PMs / Career Advice

  • As a PM, how do you go about improving your product sense or intuition?
  • What are some of the intricate aspects of product management that can either make it or break it?
  • How can you be an effective Product Manager without being that product user?
  • How do you advance in product management if companies look for you to have direct reports but your management has been via influence in a matrix role?
  • In a product management role, is it challenging being younger than many of the other people on your team?
  • What is some advice for a student considering applying for product management roles?
  • What are the hacks in understanding a software product inside out?
  • How do I defend in a product management interview that in my only brief stint as PM my websites failed & were pulled because previous CEO was a loser?

• JavaScript "Temporal" Date & Time API

  I've been helping to design the Temporal date/time API for JavaScript, which is on track to be built into browsers and Node.js starting later in 2022 and added to the ECMAScript standard in 2022 or 2023.

  I've always been grateful for Open Source. I try to help improve OSS tech with small contributions when I can. I've been doing API design for a long time, and I wanted to use those skills to give back to the community. So after I decided to step back from my startup idea, working on Temporal has been a great way to stay busy while I figured out what I wanted to do next.

  In addition to generally helping move the project forward, I did a lot of focused design work (and proof-of-concept implementations, docs, tests, etc. as needed) for easier timezone-aware code, better time duration APIs, and better Non-Gregorian Calendar APIs, as well as other smaller features. It's been fun to collaborate with a smart gaggle of OSS nerds from Google, Bloomberg, Igalia, and others to make the world a better place for dates, times, and calendars! ;-)

• Stack Overflow

  I sometimes use answering questions on Stack Overflow as "Nerd Tourism" to keep my technical skills up to date. For example: TypeScript, jest, and create-react-app, Virtual scrolling in React, MySQL query optimization, Apache ActiveMQ queue APIs, TCP socket I/O in C++ on Linux, ASP.NET data binding, CSS workarounds for Internet Explorer, HTML screen scraping, cross-platform web frameworks, and more.

other Justin Grants

• Looking for Justin Grant, Bay Area software nerd? You're in the right place! Otherwise...
• Looking for Justin Grant, IT security expert who used to work at the CIA? Try linkedin.com/in/justin-grant-67065652
• Looking for Justin Grant, swanky fashion photographer? Try justingrantphotography.com
• Looking for Justin Grant, singer of country anthem "Drink More Beer"? Try spotify.com/artist/3rHXFbeFZEnz2MOgsclsP5
• Looking for Justin Grant, new-age guru? Try justinsgrant.com
• Looking for Justin Grant, race-car driver? Try facebook.com/JustinGrant40