PODCAST 95: How to Nail Your 1-on-1s w/ Matt Cameron

This week on the Sales Hacker podcast, we speak with Matt Cameron, Founder and Managing Partner of SaaSy Sales Management.

Matt is a New Zealander by birth, an Australian by accent, and adopted American. He’s worked at Salesforce and Yammer, acquired by Microsoft, before founding SaaSy. SaaSy Sales Management runs in-person, public, and private workshops to teach go-to-market SaaS leaders how to produce the best outcome for their company and their people.

If you missed episode 94, check it out here: PODCAST 94: Expert Management of a Remote Sales Team w/ Ellie Tamari.

What You’ll Learn

  • Getting your one on ones right by asking these 5 questions
  • Lessons Matt learned from kickboxing that apply to business
  • Founders should move to the region where they want to expand into
  • Advice about goal-setting for people who are new in their career journey

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Show Agenda and Timestamps

  1. Show Introduction [0:05]
  2. About Matt Cameron & SaaSy Sales Management [1:07]
  3. Advice on How to Train [3:48]
  4. How to Nail Your 1-on-1s [5:57]
  5. Business Lessons from Kickboxing [15:27]
  6. Staying True to Yourself [19:54]
  7. Expanding into New Regions [24:45]
  8. If You’re New in Your Career Journey… [30:56]
  9. Sam’s Corner [38:49]

Show Introduction [0:05]

Sam Jacobs: Welcome to the Sales Hacker Podcast. Today on the show, we’ve got a good friend of mine and the managing partner and founder of one of the top sales training firms called SaaSy Sales Management. Matt Cameron is going to be talking to us about how to manage remote teams internationally, how to run an effective one-on-one, the number one reason that most sales processes fail, and how to think about managing your own crew (using the metaphor of yachting). So it’s a great conversation, it’s an authentic conversation

Now before we get there, we want to thank our sponsors, Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.

Now, without further ado, let’s listen to this interview with Matt Cameron.

About Matt Cameron & SaaSy Sales Management [1:07]

Sam Jacobs: We are delighted today to have on the show a good friend and one of the thought leaders and the key trainers, consultants, experts in the high growth ecosystem, Matt Cameron. Matt’s the founder and managing partner at SaaSy Sales Management, which runs in-person, public, and private workshops to teach go-to-market SaaS leaders how to produce the best outcome for their company and their people. Matt is a New Zealander by birth, an Australian by accent, and adopted American. He’s worked at Salesforce, Yammer, acquired by Microsoft, amongst a bunch of other places.

Matt Cameron: Sam. I’m looking forward to the chat. Great to be here.

Sam Jacobs: Tell us what you do and all that other good stuff.

Matt Cameron: SaaSy was born about four years ago after I spent about 20 years working in tech. One of the biggest challenges I had as a hiring and leading manager was finding ways to enable and train my people in a way that was relevant. The training that was out there was really old school. So we work exclusively with SaaS companies so that we have a common vernacular, common experience, and we work with the go-to-market leaders, so sales operations enablement, sales management, SDR management, and small format workshops.

Advice on How to Train [3:48]

Sam Jacobs: I know you put so much work into developing these courses. At what point do you know that of course is done? What are the key elements of your training and certification programs, and how do you go about doing it?

Matt Cameron: Back in 2004 was when the first time I started thinking about this. I spent a year of my life working with the Australian government getting a training facility accredited. In that time again, fire hose type of stuff, I learned about programmatic creation of building block courses that were modularized and focusing on learning outcomes.

The way we certify people is they go online afterwards and prove that they’ve implemented what we taught them. A specific example would be, we teach them the framework, best practice frameworks, we’re building a one-on-one, and then they upload the actual agenda with links to the actual reports that they’ve created to run their one-on-ones. I think it must be pretty rigorous because only about 30% of our alumni actually get fully through certification. The people that certify, they’re disciplined, process oriented, and know that they can’t just be the closing deals on behalf of reps and think that they’re going to scale an organization.

How to Nail Your 1-on-1s [5:57]

Sam Jacobs: One of the things that you talk about is how folks aren’t doing the one-on-ones right. Walk us through the industry standard for what a bad one-on-one is versus what you teach in practice and what a good one on one is for a frontline sales manager.

Matt Cameron: One-on-one is not the time to be doing deep dives into specific deals. My perspective and the philosophy of SaaSy is that there are five areas for best practice one-on-one, and it requires you to prepare as a manager. The vast majority of managers expect the rep to turn up prepared and they do nothing because they’re too busy. A good manager has a standard set of reports and a templated approach to their agenda that has five areas.

  1. Do we understand and believe the forecast? Is there a bottoms up support for the number that the reps are forecasting?
  2. Are they doing the right thing? Activity based reporting to see how they’re spending their time.
  3. If they’re spending their time appropriately, is it effective? Where are they getting stuck? Are they good at opening new doors? Are they good at progressing the deals?
  4. How do I motivate reps to give their best?
  5. What can I do to help remove obstacles?

If you take that basic framework you can apply it to any context. When the manager turns up prepped and says, “Hey Matt, today I think it’s important that we focus on A, B and C, and I’m observing this trend and I’d like to chat it through with you and see what your perspective is.” It blows their mind because that’s not the usual one-on-one.

Sam Jacobs: It’s my hypothesis that almost all sales failures or lost deals aren’t due to poor discovery. Would you agree with that or disagree with that?

Matt Cameron: I would validate that through years of evidence. I completely agree.

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Business Lessons from Kickboxing [15:27]

Sam Jacobs: If I’m not mistaken, you are also the Australian kickboxing champion for your weight class.

Matt Cameron: The backstory is, as a kid I was picked on a lot because I moved around a lot. I was born in New Zealand, but before I was 11, I lived in the United States, and Malaysia, and Australia. So moving around schools, you had to look after yourself. At 27, I moved to Australia, I was on a strong professional path, I thought, “You know what? I’m going to take four years out and just see what I can do.”

I ended up consulting for Kingston, the first company to ever do third-party memories to IBM. I consulted for them in Australia, worked about 20 hours a week, and the rest of the time I was training. So for five years almost, I was pretty much semi-professional kickboxer and ended up being at 200 pounds, Australian amateur kickboxing champion, which actually taught me a lot of good lessons that I took into enterprise sales in the year subsequently. It was not long after that I was at Salesforce.

Sam Jacobs: What are some of the lessons that you took from it?

Matt Cameron: I used to have this anxiety and paranoia that every minute I was resting, my opponent was training. If you think about that, if I’m doing large deals and enterprise, I never feel like it’s finished. I can do a better job on the proposal, I can do a little bit more research, I can spend more time building relationships. I just have this paranoia that if I’m not doing it, someone else is doing it. So that kept me high velocity in terms of my energy levels.

The second thing was, I always assume I’m losing until I win. You get in a ring with some guy, you’ve got to believe you’re going to win, otherwise you get scared and run away. But you leave it all on the mat. What that meant was, for me, chasing deals at Salesforce and whatnot, it meant that the hours were put in. If I lose a deal, it’s not because I didn’t give it everything I’ve got, it’s because I wasn’t good enough. It’s okay to lose a deal if you’re not good enough, it’s not okay to lose a deal if you didn’t put in the effort.

Sam Jacobs: Do you feel like your mindset has that impacted your ability to find peace and happiness in the rest of your life?

Matt Cameron: 100%. When I did the biggest deal I’d ever done, I was filling out RFP stuff in the hospital as I was waiting for my daughter to be born. It’s a cliche to say it, but we can make more money, we can’t make more time.

RELATED: Coaching Salespeople into Sales Champions

Staying True to Yourself [19:54]

Sam Jacobs: So you worked at Salesforce in the early 2000s, and you worked at Yammer before they were acquired by Microsoft. What were your main takeaways and conclusions from moving up through the ranks at such an important company at the time that it was becoming important?

Matt Cameron: The best companies concentrate talent. So at that time there was a guy called Jim Steele, who’s over at Yext now, who just brings his squad with him wherever he goes. There’s trust, there’s empathy, and there’s a focus on execution. So what it was like back then was zero tolerance for not doing what you say you’re going to do, and everybody having an extremely high bar. They did an incredibly good job of bonding us across departments, across geographies, through their volunteering program, and I’ve taken that everywhere I’ve gone since. It doesn’t matter how big the organization is, if you can find a way to bond people through giving and philanthropy, you’re going to have a better experience for everybody and you will attract the right talent.

Sam Jacobs: There’s not one way to be successful. There’s multiple ways and that’s why it’s so important that you stay true to yourself. You’ve mentioned to me, doing the right thing is always the right thing. I’d love to hear some examples where that’s been put into practice over the course of your career.

Matt Cameron: I’ve been in several Silicon Valley startups where senior executives including the CEOs will say whatever they need to say to get the outcome they’re looking for. I’ve been put in a situation personally a couple of times where I could toe the line and just tuck in behind whatever’s being said, or say, No, I can’t be a part of that. I worry that some young folks get coerced into aligning with views that they don’t agree with, or behaviors that they don’t want to accept around misrepresenting capability or situations or covering over bad behavior.

Expanding into New Regions [24:45]

Sam Jacobs: If I’m a small company listening to this right now, what are the key things we should be mindful of as we look to expand internationally and into new regions?

Matt Cameron: You have to take someone from HQ, put them in region for some period of time. Oftentimes I see six months or a year as a tour of duty to be the feet on the ground that helps hire and ingest new people in a way that’s consistent with company culture and gets them up to speed quickly. Typically it’s a person who’s on the rise and an investment that they make in their own career is to do the tour of duty, and make the mark by spinning up a new region, and then coming back to HQ, picking up a more senior role. For very, very small companies, typically it has to be the founder. Build the relationships I need and make sure things are set up correctly.

Sam Jacobs: If the founder listens to this and says, “I hear you Matt, but I don’t think I can go off to the new region and live there for 6 to 12 months.” What’s your response to that?

Matt Cameron: I think you can struggle. I think you need a strong number two, who looks after engineering and you need to be okay with getting up late hours at night. There are dozens of examples which say you don’t need to physically be in the same office to make an engineering team successful, not with today’s technology.

I’ve spent most of my time in that situation where your boss is in HQ, and then you have weekly get-togethers with the regional heads to make sure you’re aligned. Then we can represent a common front to HQ for the resources that we need.

If You’re New in Your Career Journey… [30:56]

Sam Jacobs: What is your advice for people as they’re setting off on their career journey in terms of how to navigate their career? What are your pieces of advice for people that want to follow in your footsteps?

Matt Cameron: Be narrow and focused in terms of what you are going to be top 5% at, what are you going to be absolutely excellent at, and stick a timeframe on it for recognition. I’ll give you a specific example. So in 2010, I came to the States and I said, “My objective within five years is to be considered a thought leader in B2B sales in Silicon Valley.” State the goal, and then figure out what it means… quantify it. I need to get known by the people that can support me in that endeavor.

When I came to the States, I set myself a weekly objective of in-person, live meetings. I just went to everything and tried to meet people and help them. So the universal advice I can give you is this, find the communities that matter to your career.

Sam Jacobs: Most people would say, “I’m happy to figure out what I want to be top 5% in, but I don’t know what that is.” So how long do you think people have before they have to have an answer?

Matt Cameron: I started off life as a computer engineer heading in that direction and then someone said marketing. So I took the foundation of computer engineering, added marketing to it, and became a really good technology sales person. What I say to you is build off your foundations. Don’t throw anything out and start again. You don’t have to know what you’re going to do in 20 years time, but you can figure out what you’re going to be really good at in 5 years time. If you want to differentiate, it’s by combining one or two things.

I think about careers as being tack left, tack right — if you’re thinking from yachting terms — and making sure that you combine some of your background education and experience in a way that’s unique to you to get ahead.

Contact Matt on LinkedIn. He loves to talk about B2B sales, SaaS, and career development.

Sam’s Corner [38:49]

Sam Jacobs: Welcome to Sam’s corner. Great interview with Matt Cameron. A couple of things we talked about, one of them is this concept of the one-on-one. He said managers need to do the work themselves of coming to the one-on-one prepared. We need people to do a little bit of work to show that they care about the people that they work with but also that they understand what’s happening within their own business.

When it comes to your career, Matt mentioned this concept of a yachting metaphor, which is tacking in one direction and then tacking in another direction, but accumulating and compiling the skills along the way so that at some point in time you can be the world’s expert in this unique combination of skills that you developed.

Don’t miss episode 96 next week!

I hope you enjoyed the show. Before we go, let’s thank our sponsor, Outreach, the leading sales engagement platform.

If you have any feedback, you can reach me on LinkedIn. If you haven’t rated the show, please give us five stars on the iTunes rating system so that we can remain in business and continue to bring you this show.

As always, thanks so much for listening, I’ll talk to you next time.

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