Some people erroneously believe that, in Startup Land, pg refers to Paul Graham. But that’s actually not correct. It actually stands for Paul Gassée.

Paul has been a startup founder, an investor, and a sales leader. And for the last 16 years(!) he’s been advising startups on their sales effectiveness.

He worked with us at Wefunder for a number of months last year, and was incredibly helpful in sharing best practices, principles, tips and tricks.

This was a super fun conversation, which covered a wide range of sales topics.

I asked Paul about how you know, as a sales leader, whether a particular strategy is working. Maybe you’ve been trying it for 6 months, there’s some green shoots of growth, but it’s definitely not a slam dunk. Should you keep doubling down, and hope that momentum continues to build over time? Or how do you know when to cut and run?

I loved Paul’s one-word answer: “Judgment”.

Then I asked him what are some of the mistakes that he finds his clients making, when he comes to work for them.

His answer:

(1) Over-doing Product-Led Growth (PLG). Paul has seen a number of founders neglect outbound sales for too long, hoping that “if you will build it they will come”. And dwindling their runway in the process.

(2) Not understanding whether the problem is “the product”, or sales / go-to-market effectiveness.

(3) Selling your product is just not enough. When you are on a sales call, you might have the client’s undivided attention. But two days later, you might have lost their attention. So you need to keep earning their attention through the sales process. And “controlling the sale”.

I’ve been reflecting a lot recently on the power of expectation setting.

Let’s say there’s a founder who, by hustling for a month, can raise $500K on Wefunder from their customers and community pretty easily. But if she wants to raise $2 million, that’s going to be really really hard. If I chat with her ahead of time and say “Oh yeah it should be super easy to raise $2 million! No worries!” — when she only raises $500K in the first month, she is going to be very very disappointed in her experience of Wefunder. Net detractor. Bye bye referrals. Bye bye growth.

But if I chat with her ahead of time and say “Well that sounds like a stretch. But maybe shoot for $250K starting out, and then you can always increase that if you are over-subscribed” — when she raises double what I had set her expectation at, she will be over the moon! Delighted customer. NPS of 10. Referral-driven growth!
And the only thing that was different in those two scenarios was that I set different expectations in each one. She raised the same amount of money in each scenario. She put the same effort in. But because of a difference in expectation setting, she shifts from an irate net detractor, to a delighted net promoter.
Shout out to Justin Renfro on Team Wefunder for really embedding this principle of “conservative expectation setting” on our BD team over the last couple of years. I think it’s awesome.

But despite this rather meandering preamble, I am going to completely ignore everything I just wrote, by emphatically declaring that this podcast interview with Rory Billing is the greatest hour of content about “how to be awesome at sales” ever recorded on a microphone, in the history of the universe.

How’s that for conservative expectation setting???
Rory Billing is the Founder and CEO of The Fan’s Place, in Rory’s words “the non-alcoholic beer of sports betting”. And before starting The Fan’s Place, Rory had a number of sales roles, which we dive into.

Jeremy Barnett is the Founder & CEO of Rad, a platform that uses AI to improve the ROI on influencer marketing.I’ve known Jeremy for a while, as he has run several Wefunder community rounds down the years, and I’ve always been impressed by his mad sales skills.In this episode, he talks about how he significantly accelerated Rad’s growth in the last 6 to 9 months, by making two key changes to the sales process:Firstly, Jeremy and the team re-worked the sales demo — to show their AI working. I think this is a very powerful point, which has wide application in all manner of sales. Oftentimes when you’re trying to sell something — especially something that is complex, or abstract — it can really help to communicate the “vision” or the “value” by making it tangible, and bringing it to life. Don’t tell. Show.Secondly, Rad’s sales team started much more aggressively qualifying leads upfront. And getting as many stakeholders looped in to the discussions, as early as possible. “We used to pussyfoot around all that stuff. And we don’t do that any more. We’re really really intentional now.”
I ask every Closing Time guest to articulate what they think makes someone awesome at sales. Jeremy highlighted three principles:(1) A ridiculous amount of persistence. This has been a recurring theme in almost every Closing Time interview to-date. And Jeremy highlighted how persistence can be manifested in multiple ways:

• “Persistence is trying to solve the problem with very intentional feedback”.
• “Persistence is pushing really really hard to get the product in a place to where people are going to buy it”.
• “Persistence is not giving up because the first couple of customers that bought the product had a bad experience”.
• More generally, “Persistence is doing what you need to do to break through”.

(2) Being an incredibly good listener. And not just listening, but understanding. And having the emotional intelligence — both to pick up on hundreds of social cues and respond to them; and also to “lead” the customer through the sales process.I thought it was really interesting how Jeremy used the word “leadership” in talking about excellence in sales. I had never thought about that word pertaining to sales before. But I really like it. I might even go a step further — and say that not only is great sales leadership, but a lot of great leadership is sales! For example, selling the team you’re leading on your vision, and your plan for achieving that vision. I imagine there’s a very high correlation between “great leaders” and “great sales people”.(3) Numbness to rejection. This is another recurring theme on Closing Time. Jeremy even took it a step further, and said that he is also pretty low-key about the wins (which is a little more controversial I think). He gave the example of LaDainian Tomlinson, who I think was a Point Guard for the Los Angeles Saltpackers, or something like that. (OK fine. He was a Running Back for the San Diego Chargers). Apparently, LDT eschewed extravagant celebrations when he scored a touchdown. He just calmly passed the ball to the ref. No drama. “This is just what I do. I score touchdowns. What’s next?”


Thanks to Jeremy for coming on the podcast. You can find him on LinkedIn here.

Will Wissing is the Sales Lead at Pinwheel, where he’s been for the last couple of years. He started his career with an exterior painting company, but after a few years doing that, he transitioned to tech sales — at MRI Software, Blend (a VC-backed digital lending platform), and Pinwheel.

Like me, Lauren McCullough did not begin her career in startups, but she found her way here after getting bored by the bureaucracy and red tape of larger organizations, and asking herself (in her words) “Like, why am I mad all the time?!” This impatience for inertia is also “probably why [she’s] never done enterprise sales”. Instead, she’s been focused on the SMB (Small and Medium Business) segment.

Recently, Lauren founded Tromml, a B2B SaaS platform that helps automotive sellers improve their eCommerce performance. Before Tromml, for several years, Lauren was a fractional sales leader at several startups. She found herself coming in to help early-stage founders solve a recurring problem — that the first sales leader they hired just didn’t work out well.

At this point, Lauren rode in on her magnificent horse and gallantly saved the day. (That is, she helped get growth going, wrote the sales playbook, hired the first Account Executive, and rode triumphantly off into the sunset.)

On this week's episode, I interview my friend Zack Turner — who's a Vice President of Enterprise Sales at Slack. Me and Zack go way back — we worked together at Kiva.org in San Francisco back in the day, and he was a groomsman at my wedding back in 2010! And he's worked in enterprise sales for almost as long as that — first at Box (he joined back when it was still called Box.net), and more recently at Slack. He's worked both as a Sales Engineer, in "frontline sales", and as a Sales Manager.

My friend Justin leads Revenue Based Financing at Wefunder (where I also work), a platform that helps startup founders raise capital from their customers and community, as well as VCs and millionaires.

Me and Justin have known each other for over a decade now. After starting his career in sales at LinkedIn, Justin very quickly got bored, and came to volunteer at Kiva.org in 2012, where I was leading the Kiva U.S. team. Over the next 5 years, we co-led that program together in San Francisco, before Justin left to start his own boat charter business in San Diego — Chill Charters (enter "Closing Time" at checkout for a 20% discount. Not really… Will probably make this dad joke every week. Apologies in advance…). In 2019, we reunited at Wefunder, where we co-lead the BD team. Justin is — literally — the best BD person I have ever worked with. And I've probably worked with hundreds at this point, so that's a large sample size! He has an incredible genuineness and authenticity, that shines forth in everything he does. But even though he's usually decked out in tie-dye, and seems to spend about 97% of his waking minutes playing frisbee golf, he's perhaps the most ruthlessly organized person I've ever met. Although not through a "CRM". He has his own system. Even with systems, Justin is a renegade cowboy :)

My friend Josh is the CEO and Founder of Salesdash, a CRM for the freight and logistics industry. Prior to Salesdash, he worked in sales roles at multiple companies, including becoming one of the top 10 sales reps in North America for Tesla. And now — perhaps the apogee of his career to date — he’s the first guest that I interviewed for this nascent Closing Time podcast :)