Aug 21, 2017 · 38m · saastr
Three Non Obvious Lessons Learned Selling to SMBs with Xero and Friends
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this expert panel hosted by Xero, software leaders from TSheets, PayPal, and Vend share non-obvious strategies for building, marketing, and scaling SaaS products for small and medium-sized businesses. The discussion highlights the importance of focused point solutions, continuous empirical validation, partner ecosystems, and authentic customer empathy.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 3.8 Guest teaching 5.2 Guest disagreement 1.2 Jason pushing back 1.2
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 35:18 Calling out fake NPS metrics
Matt forcefully warns founders against generating vanity Net Promoter Scores, pointing out that companies deceive themselves when using NPS purely as marketing propaganda.
Hardest push from Jason ▶ 19:20 Host pressing on geographic talent requirementsGohman specifically challenges whether high-end digital marketing and analytical talent can realistically be acquired outside of Silicon Valley hubs like San Francisco.
Biggest teaching moment ▶ 8:09 Lean analytics turnaround lessonMatt educates the audience and panel on how vague intuition almost ruined his startup before rigorous analytical hypothesis testing rescued the company.
Jason holds their own ▶ 16:17 Framing contextual marketing within SMB workflowsGohman synthesizes the debate around search intent versus direct problem solving to frame how SaaS providers must target contextual moments of need.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Designing Specialized Products and Finding Market Fit | 4 | 5 | 1 | 1 | Gohman sets up the opening prompt on balancing broad market fit with specialized SMB needs. Matt and Alex explain why narrow, best-of-breed focus and ecosystem integration outperform attempting all-in-one platforms for small businesses. | |
| Validating SaaS Hypotheses Through Lean Analytics | 4 | 6 | 2 | 2 | Gohman probes testing methodologies, prompting Matt to recount TSheets' turnaround using lean analytics and homegrown tracking dashboards. Alex adds a cautionary note warning against letting pure data analysis paralyze bold creative intuition. | |
| Reaching SMBs Through Empathy and Contextual Marketing | 4 | 5 | 1 | 1 | The panel explores contextual marketing and customer empathy. Alex highlights understanding small business owners' schedules and pain points, while Matt emphasizes addressing fundamental labor management concerns. | |
| Hiring Diverse Talent and Leveraging Human Sales | 4 | 5 | 1 | 2 | Gohman questions hiring location advantages and the necessity of human sales reps in an automated analytics world. Matt and Amit advocate for hybrid models, detailing past failures with pure outbound cold calling. | |
| Driving Customer Engagement, Education, and Retention Metrics | 4 | 6 | 2 | 1 | The discussion covers engagement tools, customer education programs like Vend University, and the reliability of NPS. Matt warns strongly against fabricating vanity NPS figures that misinform strategic product choices. | |
| Final Lessons on Culture, Feedback, and Customer Empathy | 3 | 4 | 0 | 0 | In the concluding segment, each panelist provides a concise takeaway regarding culture, open customer feedback loops, and treating users with human empathy. Gohman wraps up the panel collaboratively. |
Statements from this episode (13)
Gohman: TSheets has 40,000 customers, 500,000 users, and 200 employees
“Matt is the CEO of TSheets. Now TSheets is a time tracking and a scheduling software, and Matt is really in a growth phase. 40,000 customers as well as 500,000 users. About 200 employees out of Boise, Idaho.”
Gohman: PayPal has 197M consumer relationships and 15M small business accounts
“A couple of you might have heard of PayPal, an online payments provider and definitely at scale, a hundred and ninety seven million consumer relationships, fifteen million small business relationships, About six million of those in North America alone. And Pay…”
Gohman: Vend supports roughly 20,000 stores with 200 employees
“Vend is a software focused on POS for the retail segment, so a very verticalized strategy focusing on helping businesses Build, ah, build and thrive there in their organizations, but also have more fulfilling lives. About 20,000 stores and about 200 employees …”
Rissell: Best-of-breed point solutions with seamless integrations will win in SMB SaaS
“The ones that I actually think are going to win in the marketplace are those that solve, ah, one problem. They're the best in breed solution. And then what they do is they seamlessly integrate with, ah, other applications that provide a solution.”
Fala: Vend pivoted away from hospitality POS to focus on inventory-based retail
“So for us, that was saying, we're no longer going to be hospitality pause, we're going to focus completely on inventory based retail.”
Mathradas: Most of PayPal's 18,000 employees work in customer support and sales
“Kara, you mentioned we have 18,000 employees, but most of them actually sit in, you know, the customer support and sales.”
Rissell: TSheets suffered four go-to-market failures and ran out of money
“I mean, we had four miserable go-to-market failures, like to the point where we ran out of money, we had to move into free space, we had like four and a half employees, like the world was coming to an end.”
Fala: Over-indexing on analytics and NPS surveys makes SaaS companies boring
“The thing I would add to some of what Matt said is you have to be really careful that that bias towards being analytical doesn't make you boring. It still means you've got to try new things, right? So you get really analytical, and then the natural tendency is…”
Fala: Selling SaaS to retailers requires conducting product demos after hours
“Like, our customers are focused on running their retail business during the day, which means you have to do demos after hours. Like, those basic insights can have material impact on the business.”
Rissell: TSheets has no management titles across the company
“We have no management titles inside of TSheets at all, because I think managers are, like, trying to constrict and trying to manufacture authority, right?”
Fala: Salespeople cost 50% more in the San Francisco market
“You have to pay 50% more for a salesperson in this market.”
Rissell: Outbound sales failed to scale at TSheets
“Like, it couldn't be an outbound sales team that created the demand, and so that, that, that was, didn't work. So now our salespeople are different, right? So we have those that come in, and they actually sign up for TSheets, and then we have salespeople engag…”
Rissell: Manipulating NPS scores for marketing leads to bad internal decisions
“One thing that I will say is the NPS score, I mean, you will be tempted to create a bullshit NPS score. You will. You'll be tempted to do it, because it's something that you control how you do it internally, and then people leverage that as a marketing tool so…”