Show notes
After a decade building Sendoso into a category-defining platform for B2B gifting and direct mail, Braydan Young is back with a new venture—Slash Experts—that’s taking on one of SaaS marketing’s biggest challenges: converting traffic without relying on the tired “Book a Demo” CTA.
In this episode, Braydan joins Mark Evans to talk about the evolution of personalization in B2B, how Sendoso capitalized on perfect timing and deep buyer pain, and why he believes the next wave of sales and marketing will be fueled by peer-to-peer trust and real conversations.
He shares lessons from scaling a startup through hypergrowth, raising $160M (including from SoftBank), navigating culture through the chaos of rapid hiring and remote work, and the “aha” moment that made him leave it all behind to start fresh.
If you’re thinking about how to truly differentiate in a crowded market—or wondering whether your next big idea is worth pursuing—this episode is packed with insight and inspiration.
From the conversation
How Coffee Sender became Sendoso
Braydan Young is the cofounder of Sendoso and now the founder of Slash Experts. Sendoso began as Coffee Sender, a side project for sending Starbucks gift cards attached to sales emails. It reached account-based marketing teams just as they were looking for a way to stand out from high-volume email.
Requests soon went beyond coffee. Customers asked for DoorDash and Dunkin' Donuts, then for physical items. Braydan and his cofounder rebranded, added more e-gifts and set up a warehouse after meeting someone in Vegas who ran one.
Braydan says the demos worked because of one question. He asked prospects whether they did holiday gifting, and when he followed up by asking about the ROI, they said they had no clue. Gifting was common, but nobody tracked it.
Sendoso's edge was that it plugged into tools like Salesforce, Outreach, SalesLoft and SurveyMonkey, so reps could send a gift from a contact page without logging in elsewhere.
"We don't wanna be a platform of record. We just wanna plug into the tools where you already are."
The four signals that the idea had traction
Braydan describes four signals. First, the one company already doing physical sending would not partner with them, which suggested they were chasing the right thing. Second, Coffee Sender brought in $60,000 in revenue in its first month, even with margins of about 1%.
Third, Capital One came in as an early inbound lead. Braydan did not close them until years later, but it showed that big companies would take meetings. Fourth, a deal closed in Salesforce without him involved and later renewed, which convinced him the business could scale.
Selling first and raising from the right investors
Braydan and his cofounder Chris both came from sales, so they sold the product before it fully worked. When a prospect asked about an integration, they said yes, then had about two weeks to build it. With no technical cofounder and engineers based abroad, they relied on wireframing. A couple million in sales in the first year helped answer investors' questions about the missing technical cofounder.
They pitched VCs from day one, mainly to collect feedback, and heard some harsh criticism. Braydan's advice is to take the feedback that matters to you and ignore the rest.
He also says to raise from investors who know the space where your ICP lives. Storm Ventures, which had backed Marketo and Engagio, opened doors to early marketing customers. Later investors included Kraft Ventures, Oak Ventures and SoftBank, and the company raised $160M in total.
The SoftBank money arrived in the middle of the pandemic, and the message soon changed from grow as fast as possible to grow responsibly.
Hypergrowth and keeping culture intact
After the big rounds, Sendoso was hiring about 60 people a month and onboarding ten to twenty customers in the morning and again in the afternoon. It tripled its warehousing over a couple of months. Braydan says it was exciting, but growth was so fast that the team could barely keep track of who was being hired.
Culture was hard to hold together. Even the San Francisco and Scottsdale offices felt different, and later offices in Europe and Pakistan added more variation, followed by remote work during COVID. Braydan says weekly all-hands meetings and transparency became essential.
Employee eNPS surveys showed the company had slipped on values, with staff asking what they were working toward.
"You have to have your leaders actually living those values and showing you in person those values."
Why Braydan stepped back and what Slash Experts does
Braydan knew it was time to step back when he sat in the same meeting for the fifth time and kept saying, "We tried this in the past." He felt he was shutting down ideas rather than contributing. He moved to a PLG product, then began looking for his next project about a year before the interview.
The idea came from a problem inside Sendoso. The site had a lot of web traffic, but not everyone wanted a demo. Slash Experts lets a company list customers on a page such as sendoso.com/experts, where a prospect can book a fifteen minute call with a happy customer instead of talking to sales.
Customers are paid for their time. For SMB customers it is about $200 in cash or an Amazon e-gift. For enterprise customers it is a donation, such as $250 to the SPCA. Calls can also be transcribed and fed into the CRM so marketers can spot patterns. Braydan's hypothesis is to take the expert network model of GLG and AlphaSights and apply it to B2B software.
The problem with Book a Demo and early results
Braydan says the demo button suffers from misaligned incentives. Marketing wants MQLs to pass to sales, and sales may not understand the prospect well. The product can end up stretched to fit the buyer's needs, then handed to customer experience, and it may churn or become shelfware.
PLG has its own problem, since free users keep getting pinged to talk to sales. Review sites raise the question of trust. Buyers usually ask peers whether a tool works, and Slash Experts tries to capture that conversation on the vendor's own site.
Mark Evans pushed back on whether customers will give up their time. Braydan points out that sales teams often lean on the same one or two reference customers, who rarely get thanked and can burn out. Tracking calls and limiting them, for example to one a month, is meant to fix that.
About 20 customers were using the product, which is free for roughly the first six months. The default is one call a week, and some people take more. Sales reps and account managers are the biggest users, often sending a link after a first demo when a prospect wants to talk to someone who uses the tool.
"I think the typical problem is incentives are off. The people that are trying to get you to go to a website and book a demo is marketing."
Lessons Braydan is applying the second time
Braydan names three lessons. The first is not to hire for every role. Slash Experts has three people and asks whether an AI tool or outsourced service can handle a function before hiring. The team now tracks revenue per employee, which Sendoso never did.
The second is organization. Braydan says he is not a process person, but his cofounders are. Tasks live in ClickUp, contracts and records sit in the CRM, and documents come from Clerky and HubSpot, so a funding round does not turn into a scramble.
The third is to grow with the right customers. Sendoso took on enterprise companies too early, and Braydan says that can reshape the product roadmap around one large buyer. This time Slash Experts is starting with SMB and mid-market companies.
"You bring in these companies that really change your product roadmap because you're trying to solve for that big company."