Skarstad joined Airbnb Experiences just after launch as its first on-the-ground PM, helping the team search for product-market fit and a path to scale. The unusual challenge was that the product team had to shape both the booking interface and the live event a guest encountered, adding a physical-world layer that ordinary digital product work does not carry.

She joined after the initial concept and launch, before product-market fit
The team owned the digital booking journey
It also had to influence what happened when guests attended the live event
The physical experience added another layer of product complexity

“I was the first boots on the ground product manager and really helped that team figure out, you know, how do we get product market…”
Nickey Skarstad

“it's not just influencing the digital product, but it's actually the consumer experience when their boots are on the ground.”
Nickey Skarstad

#airbnb#marketplaces#product-market-fit#service-design

Story· 3

Story

How Customer Intimacy Moved Skarstad From Etsy's Forums Into Product

Skarstad joined Etsy's community team in 2010 as a forums moderator and seller education specialist, not as a technologist. Her detailed understanding of sellers made her a valuable voice in product meetings, and a VP encouraged her through her engineering-related imposter syndrome into an associate PM role; she eventually left Etsy as a product director.

She entered Etsy through community moderation and seller education
Close exposure to sellers gave her a credible voice in product discussions
A product leader recognized her aptitude before she recognized it herself
She moved from APM to director during roughly seven years at Etsy

“I worked as a forums moderator and then as a seller education specialist.”
Nickey Skarstad

“he uh gave me a little nudge and was like, I think you'd be really good at it.”
Nickey Skarstad

#career#product-management#customer-insight#etsy

Story

The Leadership Lesson of Hiring a Team, Then Having to Lay It Off

At The Wing, Skarstad spent a year hiring a technology team to bring the value of its physical coworking spaces online. COVID devastated the physical business and compounded existing cultural problems, forcing the work to pause and Skarstad to lay off the team she had assembled, an experience she describes as a major leadership lesson.

The product aimed to scale offline networking and opportunity beyond physical spaces
The role included forming a strategy, finding product-market fit, and building the technology team
COVID directly undermined the coworking company's principal revenue source
Skarstad had to unwind a team she had spent a year hiring

“COVID was pretty horrible for you know what they were trying to do.”
Nickey Skarstad

“I actually spent a year hiring a team and then had to lay them off, which was a great lesson in leadership.”
Nickey Skarstad

#leadership#layoffs#the-wing#covid

Story

Etsy Was Building With Its Community Before It Had a Trendy Name

Skarstad remembers Etsy involving its passionate seller community early because launches would not land well without them. Prototypes, beta tests, and feedback did more than improve features: they created users who could evangelize the product and teach others how to use it.

Etsy's early community was unusually engaged and vocal
Teams used prototypes and beta tests to involve sellers before launch
Community participation reduced the risk of changes landing badly
Early users helped evangelize and educate others as the product scaled

“they had such a passionate, involved, engaged early community that they could not just ship things and have them land well if they did not…”
Nickey Skarstad

“it really helps scale, get people to evangelize what you're building, help teach other people how to use it, things like that.”
Nickey Skarstad

#community#etsy#beta-testing#product-development

Takeaway· 3

Takeaway

Before Forcing Alignment, Find Out Why the Decision Does Not Resonate

Drawing on Chris Voss's negotiation approach, Skarstad argues that product leaders should listen for the reason a team rejects a strategy or goal and reflect the concern back. Empathy can reveal how to guide the group toward alignment, but it can also reveal that the PM's original decision was wrong.

Alignment problems often contain information rather than mere resistance
Repeating concerns back helps people feel heard
Understanding the objection can reveal a path to agreement
Humility matters because the PM may need to change the decision

“his whole approach is like empathy.”
Nickey Skarstad

“if you can spend some time just listening to your team and really understanding like why is this not resonating, you can help guide people…”
Nickey Skarstad

#empathy#alignment#negotiation#decision-making

Takeaway

Remote PMs Must Replace Invisible Hallway Context With Visible Updates

Remote work removed the whiteboard follow-ups, quick post-meeting syncs, and informal encounters product managers once relied on to keep teams informed. Skarstad recommends shifting routine communication into visible asynchronous channels, using lightweight audio for quick conversations, recreating workshops in shared digital tools, and resisting the urge to replace every lost interaction with Zoom.

Remote work removed many informal mechanisms PMs used to distribute context
Slack can carry asynchronous updates that would otherwise become meetings
Huddles provide a quick audio option for short stand-ups or clarifications
Miro and FigJam can replace much of in-person whiteboarding
Teams should adapt their operating style instead of filling the calendar with video calls

“trying to be asynchronous, using Slack, making sure you're following up in very visible ways where people can see.”
Nickey Skarstad

“Don't rely on Zoom meetings to fill all of your time. Otherwise, people will literally hate you.”
Nickey Skarstad

#remote-work#asynchronous-work#product-management#communication

Takeaway

A Tech-Only Feed Makes You a Worse Product Builder

Skarstad tells PMs to behave like active consumers: download unfamiliar products, use them, and follow people who interpret culture rather than only technology. Broader inputs help a builder understand the moment in which a product ships, improving the product itself as well as its messaging and marketing.

Trying new products develops product judgment through direct experience
A feed composed only of technology voices narrows cultural awareness
Cultural context influences what people want and how they interpret a launch
Broader inputs improve product decisions, marketing, and messaging

“be a consumer, to download new products, to try them out, to use all the things and try them because I think it actually makes…”
Nickey Skarstad

“You are doing yourself a disservice if your entire feed is tech people.”
Nickey Skarstad

#product-sense#culture#consumer-behavior#career-advice

Frameworks in this episode

Quality-Growth Seesaw

Red-Yellow-Green Calendar Energy Audit

Reversibility and Second-Order Decision Review

Stage-Fit Product Organization Design

Three-Check Product Review

Vision-Mission-Strategy-Objectives Pyramid

Insights & moments

✶Explainer· 1

Why Airbnb Experiences Was Both a Digital and Physical Product

❝Story· 3

How Customer Intimacy Moved Skarstad From Etsy's Forums Into Product

The Leadership Lesson of Hiring a Team, Then Having to Lay It Off

Etsy Was Building With Its Community Before It Had a Trendy Name

▲Takeaway· 3

Before Forcing Alignment, Find Out Why the Decision Does Not Resonate

Remote PMs Must Replace Invisible Hallway Context With Visible Updates

A Tech-Only Feed Makes You a Worse Product Builder

Explainer· 1

Story· 3

Takeaway· 3