Craig Minoff is an adventurer, startup leader, and strategic consultant turned product thinker who has paired a high horsepower intellect with mentorship to shape his thinking around the future of on-demand living. Today, he serves as the VP Product Management & Company Operations at flexible living accommodations growth stage startup Kasa.
He grew up in the Chicago area in a family that loved to travel. His dad was a consultant and Sears executive while his Mom was in the first class of women at Dartmouth, an old-school Product Manager who designed real-life physical products (!). When Mom came to school for show and tell, she brought toothbrush bracelets she’d designed for the kids.
Craig was a smart, talented student and set off to Yale for his undergraduate studies where he studied Economics and served as the President of the Yale Economic Review. Comfortable with travel from growing up, he set off for a semester abroad in Salamanca, Spain.
After graduation, he worked for Boston Consulting Group out of their Chicago office. He entered into a supportive partnership group in that office with a cohort of 25 or so fresh graduates, getting to start his professional career with a built-in, ambitious friend group.
At BCG he learned the power of setting boundaries around his work. The most senior and successfully tenured team members he admired who seemed to thrive were able to draw professional lines and carve out time for their own personal hobbies, friendships, communities, etc. to deliver more value for the company as better coworkers & leaders.
While Craig was at BCG, a college friend, Michael Waxman, started a company called Grouper that focused on helping groups of friends meet each other. During the meteoric rise of social media, more people were spending time online and less time meeting in person. Online dating was not quite yet mainstream. So Grouper became a fast-growing, low-stress way to meet new people with your friends.
Craig was drawn by the opportunity to apply his BCG skills in an early-stage startup setting and moved to New York to join a scrappy team of about 10 people as the Director of Growth & Business Intelligence. He experienced rapid growth and helped the company raise Series A funding. Grouper grew to about 40 or 50 people and Craig worked alongside engineers and designers for the first time, facilitating product roadmaps, completing A/B tests, and more. Learning through applied environments is a theme from Craig’s career and, instead of going to grad school, Grouper became a transformative career learning experience that drove him to optimize for rapid learning environments.
When free dating apps like Tinder & Hinge became more popular, Grouper’s growth stalled. Craig had been Airbnb’ing his apartment to make a couple extra bucks by marketing “views of the Empire State Building” if you squinted. Hopefully his landlord isn’t reading this… Coincidentally, Airbnb’s Co-Founder & CTO Nate Blecharczyk was on the Grouper board.
When Grouper went through a reduction in force through their growing pains, Craig’s parting gift was a warm referral to a recruiter at Airbnb. He landed a role at the company in 2014 in their internal consulting group to help with strategic product planning & analysis.
Airbnb was a great fit for obvious reasons. Initially, Craig got to work on classic consulting projects like running business segment analysis around entering business travel vs. bed & breakfasts vs. long-term stays or luxury travel. Of course, over the next 5 years, all of those segments became a reality! Airbnb combined the best of his startup experience with Grouper and his BCG consulting skills.
Working alongside 5-10 product leaders across Airbnb’s business, Craig led an effort to help prioritize, estimate, and track the product roadmap planning to drive better decision-making. His experience from consulting was that you can never get an estimate perfectly right, but spending the time quantifying the upside & cost is still valuable to building a more informed “business case” instead of just deferring to the H.P.P.I.O. (highest paid person in the office).
One of his closest product counterparts at Airbnb was Lenny Rachitsky, who encouraged him to consider becoming a PM. Together they wrote specs, Craig took on features within Lenny’s team, and the company eventually created an internal mobility path to product management loosely based on their work together.
Craig worked on important multi-quarter projects like making cancellation policies friendlier to guests. He got exposure to senior leadership audiences with Brian Chesky, Nate Blecharczyk & Ellie Mertz to help them compete with Booking.com and better align with broader e-commerce policies. Craig & Lenny partnered to convert the Airbnb platform from Request to Book to Instant Book.
At the time, booking requests had a 60% conversion rate. Imagine only being able to purchase 60% of the groceries in your cart when you go to checkout? It was the era in which marketplace behavior was defined and a lot of it came down to building trust through new products on the platform. Airbnb has continued to incentivize more flexible policies over time.
While he was at Airbnb, Craig had purchased a small building in Chicago with his friend Roman Pedan and a few others to run as a short-term rental business and see if they could do it at scale. Roman was interested in pursuing the idea as a startup full-time coming out of Stanford Business School.
When Roman’s company Kasa landed their seed funding, Craig joined as their Head of Product in a dozen-person company soon after. It was time to get back to the early stage with the benefit of some serious prior experience & mentorship.
In the 5 years since, Kasa has scaled to almost 250 team members and raised Series A, B & C rounds of funding. Craig is enjoying the challenging company-building aspects of startup growth aiming to develop “best in class” teams, people management, org design, and culture to instill best practices from “Day 1”.
Craig oversees Product, Design & Engineering in a traditional Head of Product role. He also oversees BizOps & Business Intelligence and rounds things out with time in company operations. There, he’s implemented processes like 360º reviews, career growth pathing & ladders for employees, and is responsible for growing Kasa’s business by helping to structure their product roadmap efforts. He works closely with Kasa’s leadership team and Chief of Staff to plan leadership summits and handle other strategic planning efforts.
Craig relocated to Boston during the pandemic with his partner. Another product leader, the two of them drove around the U.S. for a year and built a spreadsheet to find a city that fit both of their personalities. Boston won! It’s close to the ocean, the mountains, and Cambridge is always a hub of activity. We’re glad to have you here Craig!
Planning & Prioritization to Drive … Time & Attention Spend
The hardest question in work and life is, “where do I spend my time and attention?” Craig believes effective prioritization ultimately comes down to leading a strong process.
Craig is proud of the system they’ve built at Kasa for their product roadmap efforts. Like a sine curve, they spend one part planning for every three parts of execution (1:3) to make sure there is a proper ongoing ratio.
Yes, in earlier-stage startups that is harder and it’s tough to plan out 2-3 quarters. But thematically some amount of “business case” math is better than nothing. Spending 5-10 minutes on a project to determine the rough upside against the potential cost is invaluable time spent.
Craig leads his team through an exercise to build a business case against a reasonable amount of variables (10-30) each translated into a revenue figure. Then, each business segment will use assumptions around their historical conversion rates. Last, they’ll approximate the length of a “lever arm” to best estimate the impact of an initiative.
This is particularly important when weighing revenue against the cost of committing the resources. Since resources are limited in a product & engineering org, measuring commitments in “people weeks” or months as a universal form of cost helps you determine roughly sufficient ROI. It won’t be perfectly stack-ranked, but you can use the data to create a starting point and supplement that with a voting session so more perspectives can contribute to the final order.
Kasa’s process, crafted at Airbnb, is rigorous because each hour of product planning could mean 3x more design time or 5x more engineering time for a product. Investing a few more minutes, hours, or days of extra planning spec’ing and choosing deliberately upfront pays dividends down the road.
Career Insights / Learnings
Alternating Learnings – “There’s value in learning both from firsthand trial & error and through mentorship. While the mentorship lessons won’t always sink in as deeply, it’s a faster process where you can learn from the best. If you pair strong mentorship with choosing a career path based on maximum learning, I’ve found that’s a pretty good combination for success”
Tours of Duty – “One of my first managers at Airbnb taught me the concept of ‘tours of duty.’ Think about each ‘tour’ as an 18 to 30-month learning opportunity. Afterward, it could mean changing companies, functions, getting promoted, or shifting business units — but the key is to mix it up! It’s healthy and valuable from a personal energy standpoint to maintain a rapid sense of learning & growth every couple of years and I try to optimize each tour of duty to see where I can learn the most & fastest.”
Work on your Interests – “Choose an industry to work in that you spend your free time reading about. If you’re going to be reading those books anyway, might as well make it a 2-for-1 special! I thought the dating industry was fascinating, and I love to travel. Now I get to work in travel, read about travel, and travel more!”
Products Don’t Sell Themselves – “The best product still needs to be marketed. Many people take for granted that and think that just because they’re working on it, everyone else cares. The reality is that most people don’t care and it is your responsibility to remind them, regularly, why they should care. You shouldn’t assume they’re excited to read every word of your e-mail. Reduce your assumptions around user commitment. It takes part product AND part product marketing to capture people’s imagination.”
Eventually, Craig has a pipedream of starting a travel company to help bring people together through adventure & outdoors. He’d love to continue having a vocation that aligns with his interests, and if he could build a product that was a peak memory for people’s lives, how great would that be?
If you’d like to learn more about Craig you might find him traveling the world, charting the future of flexible living at Kasa, or on LinkedIn. Thanks for sharing. We’re excited to see the teams, startups, and leaders you impact in the years ahead!