Sales Pipeline Radio, Episode 199: Q & A with Jim Wilson @JimWilsonSF


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If you’re not already subscribed to Sales Pipeline Radio, or listening live every Thursday at 11:30 a.m. Pacific you can find the transcription and recording here on the blog every Monday morning.  The show is less than 30 minutes, fast-paced and full of actionable advice, best practices and more for B2B sales & marketing professionals.

We cover a wide range of topics, with a focus on sales development and inside sales priorities. You can subscribe right at Sales Pipeline Radio and/or listen to full recordings of past shows everywhere you listen to podcasts! Spotify,  iTunesBlubrry, Google Play, iHeartRADIO, or Stitcher

This week’s episode is entitled “Selling from Scratch: Foundations and Fundamentals for Building Your Sales Team”.  Our guest is Jim Wilson, Operating Partner at Costanoa  Ventures.  

We talk about the impact of the COVID19 outbreak on sales, but we also get down to some good, timeless sales team building wisdom and give you some great takeaways you can use both right now and going forward.

I love the advance of social selling tactics. I love the advance of challenger sale and the teach and tailor type mentalities. But I think in our effort to create more value as trusted advisors, a skill that isn’t being taught as much today is how to ask for the deal, how to ask for the sale, and how to close.

I ask Jim to double down on these and provide examples and ideas. You’ll love his Four Cs of Closing.  Listen in to hear his answers about how companies put more of a focus on these in the organization. He answers if this a training issue and shares the best ways for companies to get better at closing. This and MORE.  Listen in and/or read the transcript below.

Paul:  Hey, welcome back, everybody. Time to grab your board, swim out into that choppy sea out there. Right now, it’s rather confusing and chaotic, but maybe we can still catch a wave. We want to wave to Matt Heinz, who’s going to join us here today. Hey, Matt.

Matt:  How you doing, Paul?

Paul:  I’m doing good. The question is, how are you doing? You’re up in the center of the storm up there. You’re in Kirkland, Washington. All I read about is scary things in Kirkland, Washington.

Matt:  I am in Kirkland, Washington. We are recording today, Sales Pipeline Radio live from my basement bunker, the basement of our house. I don’t have a home office. I have a basement, which is kind of a man cave-ish kind of place. As I look around, I’ve got my desk. I’ve got my office set up. I’ve got a big-screen TV down here. I’ve got a little whiskey library over in the corner.

Paul:  There you go. You’re practicing social distancing as we speak here.

Matt:  I have internet access. I have a television, and I have whiskey, so I’m ready for whatever comes.

Paul:  Okay, good for you.

Matt:  Today’s conversation will be apropos because I think we’re going to talk about sales. We’re going to talk about sales strategy. We’re going to talk about getting through this together, and knowing that there is an end to this, that there will be an end to this, and there will be a rebound. We need to protect ourselves, keep ourselves healthy. Wash our hands.

I’m fortunate that I am home. My family’s home, and we’re taking care of ourselves and those in our community that need help as well.

Paul:  Well, I don’t know whether or not you realized you started a storm last week here at the station and on the channel here because you very delicately stared to jump into the issue. Maybe people weren’t ready to hear this, but what comes next after we get through this storm? Do we just exhale and go back to sales events and flying around the country like we did, or do we adapt and come up with some new strategies that either replace some of that activity or add to that activity? I think that’s a question we’re all wondering. What’s the new normal coming out of this?

Matt:  It’s a really great question, and I think the answer, and I’ll look forward to hearing our guest’s answer today as well, is I think the answer is yes. I think that we are going to rebound from this. We’re going to learn some things from this. Hopefully, we are smarter for the next time it comes around, but I think it’s also going to make some smart adjustments, create some smart adjustments and innovations to how we do business, how we work as a community, how we support each other through challenges as well.

It’s definitely interesting times. I want to thank everyone for joining us on another episode of Sales Pipeline Radio. If you’re listening to us today live on the Funnel Media Radio Network, thanks for joining us, making us part your, what is probably a work-from-home workday. If you’re listening to the podcast, thank you very much for subscribing. Very honored to have so many people who continue to listen to us. If you’re interested in any of our past episodes or future episodes, you can find them all, past, present, future at

Today, we are featuring yet another great guest, a great, smart mind in the B2B sales and marketing world. Very excited to have with us Jim Wilson, an operating partner at Costanoa Ventures. Jim, thanks so much for joining us today.

Jim:  Thanks, Matt. Thanks for having me on. I’m looking forward to speaking with you about the topic.

Paul:  And I just want to point out before you guys take off here, that he is operating from a phone booth in old-fashioned style here, isolating himself. He must be superman. He must be getting ready to reveal himself.

Jim:  That’s right.

Matt:  Now, that is a new type of social distancing that I have not yet heard, and I didn’t know that there were phone booths. This is true? Where are you today?

Jim:  Oh, I’m in the Costanoa offices in San Francisco, and we have these great sales telephone booths in the office that you can kind of wall yourself off and concentrate, and speak loudly and passionately about whatever topic you so desire.

Matt:  I think, Jim, what you had asked earlier, I think, is maybe a good question for us to start with. I think a lot of companies are sort of making adjustments right now to how they do work, thinking about what Q2 might look like as a result of what’s going on. There will be a post-coronavirus world. We will rebound from this.

I think as someone who has spent a long career in sales, sales management, and helping companies grow their business, how do you look at this in terms of what companies are doing now in the midst of this, and how do you think about how companies should prepare for the next stage?

Jim:  I think it’s a great question. I’m always reminded of the phrase, “Stay calm, and carry on.” I think it’s very applicable here. I would second what you said, which is that everyone’s going to come out fine on the other sign, but, at the same time, there is a new reality for salespeople and sales organizations they have to deal with. That first reality is that the in-person meeting for the near term is going to end, and you need to look at being as productive and as effective as ever, but in a virtual environment.

I think the second thing that people need to be realistic about is that in their pipeline, there are going to be certain industries and sectors that, in the short term, are absolutely going to affected by this virus and this downturn, in particular hospitality and travel. I’ve encouraged all of our portfolios to just take a hard look at their pipeline as it relates to forecasting and predictability, and be realistic with themselves with what’s going to happen.

Then, the third thing I would say is a point of positivity, which is this is a great opportunity to be close to your customers. Ask them how they’re doing, and build great and deep partnerships because we will come out of it better on the other side, and you want to be a positive force and not a negative force.

Matt:  Yeah. Yeah, such a great answer, and I think important to look at what you need to do now to really be focused on the business it is close at hand. Understand that some of your prospects are going to slow down decision-making. Many of those deals aren’t going to go away. They’re going to get delayed. They’re just going to pause for a while. It could be that depending on how this goes through, what could be a tight beginning of Q2 could be an amazing end of Q2.

But I think to your point about your existing customers and your prospects, a healthy level of empathy and understanding of what they’re going through is really important. The other thing I literally talking to a customer this morning. We all want to make sure that people are comfortable. They’re taking care of themselves and their families.

I had a customer this morning express some real just awareness of wanting to make sure that they were investing and accelerating at the right point as we get to the end of this, of this period, so that they’re not caught too flat-footed when the rebound happens. Is that something that people were thinking about, and what variables exactly would you look for to make sure you’re sort of accelerating ramping back up at the right time?

Jim:  I think it’s a great question. I haven’t had that conversation yet with any of our portfolio. My personal opinion is it’s probably too soon for no other reason that we don’t fully yet know the impact. Whether we know we’re at the bottom, whether the trough is going to be a V or a U, we don’t know. That said, I think that a lot of the basics still hold in terms of looking at leading indicators, which would probably most likely be engagement.

Look for events that start to come back online and be in-person. Look for business to start operating as normal, and, frankly, just be as nimble as you can be either up or down for the next few months.

Matt:  Talk of the day on Sales Pipeline Radio with Jim Wilson. He is a veteran sales manager, sales leader. He is an operating partner at Costanoa Ventures now, and a board member of many companies, including Kenna Security, which has been a client of ours very recently as well.

You mentioned sort of people that are doing face-to-face selling, how that has particularly been impacted. I think a lot of companies, especially those that might be in the software business, they’re selling through the telephone. They’re selling remotely and so that sales process hasn’t been too materially changed. Although you may have people that are working from home that you’re trying to call them, it may make things a little more difficult.

But I want to specifically talk about those field salespeople. We’ve got clients in manufacturing, for example, that count on bringing samples of their products to someone’s office. That’s obviously changing for the foreseeable future. Are there things that those salespeople can do to try to replicate the value of the face-to-face selling in a virtual environment?

Jim:  Boy, that’s a great question. Early in my career, I sold CAD/CAM software to a company called PTC, and I can’t imagine what it’s like right now for folks that really do make their sales living off of those face-to-face meetings with samples. I guess the advice I would give people like that is, number one, first, start by showing empathy, just a simple question of your prospect or client. Would you be okay meeting in person? Would you prefer something different? Just showing the classic sales technique of looking at it from the buyer perspective, I think, would go a long way.

I think second is, it’s an opportunity to be creative. Great salespeople, I think, are super creative. So is it possible to ship those samples in FedEx? Can you leave them at the doorstep with a nice note, and then tell them that you’re going to call them from across the street in that proverbial phone booth? But anything that you can do that’s creative that gives them the feeling that you are going above and beyond to take care of them, I think, will always be appreciated.

Matt:  I would agree with that. I’ve seen people that are wondering what the current period is going to do to their short-term numbers. I’ve heard some people say, “We’re going to sell our way through this. We’re just going to sell harder.” Unfortunately, I’m seeing a little bit of examples already of it turning into just most pestering, people getting what seems to be maybe a little bit desperate, price decreases, some flash sales, a few more phone calls to people that are not quite ready to buy.

On the contrary, I’ve also seen companies that are kind of doing the opposite, that are recognizing that customers may be in a similar situation, that they themselves may be pivoting. And instead of saying I want to sell you something more quickly, they’re offering help. They’re offering sort of free services. They’re offering a little more generosity as a way of not only addressing the current customer’s need but also sort of earning the business long-term from those customers.

Are there some other examples that you could think of that, in a similar way, that sales professionals and sales teams might be able to be of service to sort of reinforce the trusted advisor status for themselves with those customers for short and long-term opportunities?

Jim:  Yeah, you and I have exactly the same perspective on it. I look at things like this as less around doubling down around working harder, but more doubling down around the human element and the creative element to add more value. That can be in the form of support. I think an outreach before it’s asked on if people need support. Think of all of the industries that do virtual and digital work that are actually having the opposite problem right now. They’re probably over-burdened and worried about scale issues.

If you have those types of customers, asking them if there’s anything you can do to help. Offering up resources and services, I think, is always appreciated. Frankly, in my experience in selling, even if they don’t take you up on it, the fact that you thought about it and you did it before it was asked, it puts you in the win column with most customers.

I would reiterate what Matt said too, which is doubling down and calling people, being proverbially more aggressive is probably the wrong tactic right now. It doesn’t mean that being creative won’t get you the same results, but barge in through the front door when the door’s being locked a couple times right now is probably going to have negative consequences.

Matt:  Do you think, I know maybe from an advisor and even from a funding standpoint, do you think that this is going to have a longer-term impact on the funding market for startups? Just this week, as we see sporting leagues sort of cancel and everybody kind of shut down a little bit, still seeing some pretty large funding announcements, and, obviously, those have been in the works for a very long time. Is there going to be a bit of a shadow effect there for companies that have been trying to raise cash?

Jim:  I don’t think so. I think that this is a short-term, black swan event. Another venture firm coined that recently, Sequoia. It’s not something that is permanent downturn. I think that people that are in funding cycles right now need to probably think about their cash position more than anything else. I think the unit economics are more important than ever to companies, so your ability to spool up or spool down in short terms like this and know and understand what levers to pull, I think is super critical. Look, companies that have great products, that have great sales teams, and great founders are going to come out just fine on the other side.

Matt:  I agree. We got a take a quick break. Pay some bills. We’ll be back with more from Jim Wilson. We’re talking about selling in adverse conditions. We’re going to talk more when we get back from the break about best practices and what he’s seen working in modern sales environments as well. We’ll be right back, Sales Pipeline Radio.


Paul:  All right, back to Matt and his guest.

Matt:  I’ve been thinking, Paul. I’ve been thinking about you this week, so, like we talked about this year, we’ve talked about this idea of the predictable pipeline, and you’ve used sort of the wave of the surfing analogy for a while. The book tentatively titled, The Predictable Pipeline, I have a contract with Wiley. It’s coming out in November, so I’m excited about that.

Paul:  Wow! Congratulations, yeah.

Matt:  Thank you. Was thinking about you this week because they’re already saying, “Hey, what do you think we should do on the cover?” Internally in brainstorm, Sheena actually brought up saying, “You know…

Paul:  Got to be a big surf pipeline, that cool image of the surfer entering that long tunnel of water here.

Matt:  Yeah. Well, the analogy, I think, is interesting. I don’t know if you meant this, but I think if you think about the idea of having more predictability of the pipeline that you create, the waves continuing to crash against the shore, about as predictable as you get. They keep coming.

Paul:  Yeah. Exactly, and you never know when you enter the pipeline how long it’s going to last and what you’re going to come out on the other end. Are you going to splash? Are you going to be still standing? There’s that wonder as you enter into the pipeline itself too, so it’s both predictable and unpredictable. It has both elements to it here.

Matt:  I don’t know. Might have to connect to you. I don’t know if you have any artistic abilities, but we’re working on design, so I may come back to you on that.

We want to continue with our guest today on Sales Pipeline Radio, Jim Wilson. We’re talking about sales in adverse conditions. I want to go back and, current virus aside, to talk about just the evolution of sales. You’ve been in the game for quite a while it sounds like. You were in the field with the quota, selling devices. You’re now on the board of many companies that are offering software as a service, that are younger companies that have had the ability to, in many cases, create sales organizations from scratch.

What are some of the main themes you’ve seen from your early days of selling to today, and what are some of the really sort of most important themes and best practices of the higher-functioning sales organizations you’re working with today?

Jim:  Thanks, Matt. I’m really lucky. One, I am older and that I’ve been able to experience a lot of different companies. I’m managed inside sales teams, outside sales teams. My job at Costanoa, running and working on the operating platform, really allows me to do three things, work with people, help companies develop messaging, and help them ultimately turn that into sales.

Costanoa, specifically, works with boutique enterprise companies that are seed and series A, early-stage companies. We look for great founders that are trying to build great products and tackle huge problems. Some of the patterns that we see that we kind of preach pretty consistently are all around building the foundation for sales.

I like to talk about what does your first hire look like. How do you profile people? What’s interviewing like so that you can get the right type of salespeople? How do you balance inbound and outbound prospecting to build that predictable pipeline, Matt, that you’re going to write your book about? How do you enable the sales teams so they are effective? Then, finally, I love to just talk about some hacks around closing techniques that I’ve learned and picked up over the years.

Matt:  I’d love to hear those. That’s where I think that a lot of modern marketers are lacking in skills. I love the advance of social selling tactics. I love the advance of challenger sale, teach and tailor type mentalities. But I think in our effort to create more value as trusted advisers, a skill that isn’t being taught as much today is how to ask for the deal, how to ask for the sale, and how to close. I would love to double down on that and get a couple examples of some ideas that you think are particularly pertinent on that.

Jim:  I used to call it the four Cs of closing. This was usually the talk that I gave my sales team with about a month to go in the quarter or a week to go in the month if you were on a monthly cadence. The four Cs of closing are just a simple checklist of things that you should have and are progressing to feel good about a deal actually closing.

The first of those is commercials. Commercials is really a fancy word for saying pricing. What I used to always tell salespeople is, “Look, pricing doesn’t mean, ‘Oh, I’ve given them a quote. I’ve sent it to them, and I’m expecting them to accept it.’” In today’s selling environment, commercials are not actively being discussed unless there’s a little bit of back and forth around pricing.

The other kind of hack and trick that I tell people is best indicator that you’re entering into commercials is when they’re asking you for pricing, and they’re asking questions about it. If you sent them a quote and there’s no questions coming back, that’s not a good sign. That means you’re not really dealing with commercials.

The second is contracts. It used to be that you were able to sell deals, and if you’re lucky enough to do it to where you can just send over a pdf, and they sign it, or you have something online, that’s great. That’s not the way it works with larger order contracts and larger-sized deals. You should expect that there’s at least some questions around contracts or some red-lining going back and forth.

Then the last two are specifically around selling themselves. The first is a compelling event. A compelling event, by the way, is not the salesperson’s end of quarter. That’s the first thing I probably tell them is that the buyer, as much as you like to think it, he really doesn’t care about your end of quarter. He may care if you’re putting an incentive in place that benefits him, but no buyers that I know are sitting around wondering which sales teams have their end of quarter.

So you have to think about this customer as what compelling event, what’s compelling them to buy. Are they replacing something that’s running out of a contract you out of a contract? Do they have a gap in a problem that you’re trying to solve that your solution solves? What’s the compelling event that’s driving urgency on their side?

Then the fourth C is probably the most important, which is champion. A champion is someone who has two things. He has power in the organization, and he sells for you in the account when you’re not there. If you don’t have a champion that’s giving you feedback and telling you where you’re at in the process, you’re probably not closing that deal.

Matt:  I love those four Cs, and I think that each of those could easily be another episode of the program. I think compelling event, in particular, I think a lot of people don’t understand what specifically has created and is perpetuating the commitment to change inside an organization. What does that outcome look like? When is it needed? What’s the opportunity cost of not having it in place, and when does that start?

Understanding those things that sort of are going to keep something as a high priority to close is really important. I love that you focused on champion at the end. The challenger analogy talks a lot about having this buying committee and having multiple people as decision-makers, as influencers. Yes, we need to sort of build consensus amongst that group, but there needs to be someone, or a small group of that, a subset of that group that is maintaining that momentum and progress internally, especially with these really big deals that will take months, quarters, or sometimes, especially maybe if a federal deal, we could be talking Olympic cycles to get something done.

You, as a salesperson, are going to be hard-pressed to drive that momentum velocity on your own. I love your four Cs. How do companies put more of a focus on this in the organization? Is this a training issue? What are the best ways for companies to get better at closing?

Jim:  Yeah, great topic. So look, one of the things that I think is the hardest thing to do in building a sales organization is build a culture of learning and build a culture of sales enablement. There’s a couple things that our portfolio, that I see, does particularly well. I would call out companies like Propeller Aero in our portfolio. They have this great culture where they’re all learning, and they’re building processes, and they’re comparing notes. There’s no judgment when they do, and they’re super creative about all their ideas.

Here’s some of the things that I’ve seen they do. First, they really embrace tools as a way to help them enable and repeat best practices. I’ll give you the most simple example I can think of. Today, in this world right now, we’re going to be doing more things virtually, so we’re going to do everything through Zoom or other virtual meetings. Just start to record those. If you have a really great sales call and it’s recorded, and you can share that with the sales team and break it down, what’s working, what’s not, is great.

The second thing is we think that it’s obvious today, but you’d be surprised how many companies don’t do it, but you’ve got to put a CRM tool in place. The CRM tool is what people need to use, and it allows you to document things and learn best practices. But a tactical thing that goes with that is set up a weekly cadence and a weekly call, and dedicate a period of time for that weekly call just to be on learnings. What have you learned? In particular, focus on what did you learn that worked? How did you win? What did you learn that didn’t work? How are you losing? And what messaging is sticking?

The key I’m seeing is to keep it really simple and make it repeatable, so everybody goes around the room with what’s worked, what hasn’t worked, and some messaging that’s sticking. You encourage everybody to share. Then, finally, really focus on customers and customer knowledge. Again, I’ll go back to the buyer perspective. Most buyers today really don’t care too much what the seller has to say unless what that seller says is a customer story, it includes a metric and a value proposition of how that customer benefited from using your product.

Matt:  Well, unfortunately, we are out of time. These conversations always go too quickly, but lots of great nuggets of perspective on the current market conditions as well as some best practices on selling, and particularly, I like the focus on closing.

I want to thank our guest again today, Jim Wilson, for joining us. If you like this conversation, especially if you’re a sales leader, if you’re working with sales teams, want to share this with other people in your organization, we’ll have this episode up on-demand at here in just a couple days. We’ll also, as usual, have a transcript and summary of this conversation up on very shortly.

Join us next week. We’ve got an amazing lineup, actually, coming up here as we head into Q2 very quickly. For today, we’re out of time. On behalf of my great producer Paul, this is Matt Heinz. Thanks for joining us on another episode of Sales Pipeline Radio.

Republished with author's permission from original post.

Matt Heinz
Prolific author and nationally recognized, award-winning blogger, Matt Heinz is President and Founder of Heinz Marketing with 20 years of marketing, business development and sales experience from a variety of organizations and industries. He is a dynamic speaker, memorable not only for his keen insight and humor, but his actionable and motivating takeaways.Matt’s career focuses on consistently delivering measurable results with greater sales, revenue growth, product success and customer loyalty.


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