Achieving Excellence in Enterprise Sales with a Cross-Functional Mindset with Reid Oliver

Apr 7, 2022

Strong communication skills will serve you well in any industry, but they’re especially crucial in the sales world. Today companies are moving away from the traditional corporate structure of working in silos to adopt a more streamlined approach.

And establishing synergy among teams is really essential if you’re hoping to optimize sales outcomes and meet or exceed all of your sales targets.

On the most recent episode of Ready, Set, Sell, our guest Reid Oliver shared his tips on finding cross-functional alignment to achieve excellence in enterprise sales.

As the enterprise sales director at Splunk, Reid has found a few different leadership strategies that work for him and his team. He’s here today to let us in on all his secrets.

Who is Reid Oliver?

Hannah: Tony and I usually start by being a little bit nosy. What I’d love to do is get you to share a little bit about your career background so far — more specifically, the points that really made a difference in contributing to where you are today.

Reid Sure. I have been in software sales for seven years now. So, I’m certainly not a grizzled veteran and I still have plenty to learn. I’ve been at two companies. My first foray into sales was with a Series C company called Vidyard. We were doing B2B video hosting, data analytics, internal communications. I started there about as entry level as you can get, as a sales development representative, managing inbound leads. We had a phenomenal manager at the time and I also took advantage of a good growth curve, so I was able to move into a business development representative role as an account executive (AE). And then my final role there was with our enterprise team, selling into some of the biggest customers that we had at the time.

Addressing your question around getting to where I am today, I would recommend to anyone joining a startup early on in their sales career. You just get so much good exposure to wearing a lot of hats. Since then, I decided to move over to where I am right now, which is Splunk. I wanted to get to more large-enterprise complex-platform selling, with much larger deal sizes. And again, I’m really fortunate around timing and leadership and growth. I started as a commercial regional sales manager (RSM), an AE role, and today I’ve gone through a few different roles at Splunk because they are managing a strategic Canadian business. I’m now working with the largest customers and companies in Canada.

Tony: Excellent. I actually know Vidyard very well because I was a customer for a while. Sounds like you’ve done a great job climbing the ladder, but what drew you to sales in the first place?

Reid: A few factors. I think one of the biggest would be my parents and, in particular, my mom. She was always involved in our school and kind of thinking about careers and what would set us up for success. And part of that, we did some career kind of testing my brother and me, and one thing that always shone was that I always tended to score higher on EQ than IQ. So I wasn’t necessarily going to try to go for a surgeon or an investment banker. But pairing that with kind of playing a lot of sports, being competitive, maybe even just a general business interest, I thought that salesman made a ton of sense. And so that ended up where I ended up being, where I put a lot of my focus.

Hannah: Splunk is an awesome company. I’m actually working with a few people at Splunk over the last year. Yeah, I’d love to know a bit more about how you landed your role at Splunk.

Reid: Yeah. So it was, like a lot of roles these days, just networking. I was, as I mentioned, trying to figure out where my next step would be from Vidyard. I knew that cybersecurity and big data was a huge market still continues to be. And so I looked at who was a leader in that space, and Splunk was certainly top of the list (and continues to be), but at the time was really the key player. And so I ended up just looking up where I had connections and reaching out and having a cup of coffee with those individual sellers and one of the managers. And I ended up getting put into the interview process through that.

Tony: Well, it sounds like you’ve kind of been climbing the ladder. You started at Vidyard, you made your way to commercial accounts, and now enterprise. What would you say you like most about enterprise sales and what you’re doing right now?

Reid: I think the best part about enterprise sales is just the strategy behind it and the relationships that you build and the impact that you’re having on a customer account. I mean, enterprise deals are generally quite complex there. You need change agents across a company using multiple layers of champions across technical and key stakeholders. And so that’s certainly something that’s probably more absent in the more traditional kind of transactional selling model. I think it’s good to experience both, but the former certainly appeals to me from an enterprise perspective, and just getting the chance to be a part of a much larger deal cycle and impact from a revenue perspective to the company that you’re at is fun.

Tony: Yeah, the checks are always bigger, too, which helps. So that’s good.

Reid: This is true.

Hannah: When it goes right, that is.

Reid: Correct.

What is Splunk?

Hannah: Reid, I’m going to I’m going to try and remember what one of your company’s straplines are: is it data to anywhere? Is it something like that right for Splunk?

Reid: Data to everything.

Hannah: There we go. I was close! I’d love you to share an overview for those listening who don’t know what Splunk specializes in because I saw some material beneath the surface and I thought it was really cool. I’d love for you to help us understand how you help businesses grow and improve their outcomes.

Reid: Sure. In an analogy that I heard early on — and we’ve certainly grown from this — but we used to be kind of Google for IT. We were the de-facto platform to help IT professionals and security professionals dig through massive amounts of data and get to their answers quickly.

And from there, we’ve certainly developed into still being that critical query and big data ingest platform but we’re now turning also into visualizations, alerting orchestration and automation, and obviously applying layers of machine learning across these massive complex datasets. So ultimately, we’re helping security professionals ensure that their products and their companies are secure and identify when issues happen and where they are really quickly.

On the IT and DevOps side, we’re helping folks ensure that their websites are up and running and we’re ensuring that if bugs and issues are happening, they’re finding the root cause very, very quickly and, oftentimes, doing that through a predictive model rather than reactive. So it sounds like it’s a really sophisticated process there that you guys have to go through. And I’m curious about the different teams that you have to engage with on the sales side. So, you know, as you’re going through your process, what are the different teams that you typically engage with? How do you do that? And you know, how do you make sure that everything is working cohesively together?

Yeah, it’s not uncommon for our win notes on big deals to span multiple pages, and then you have to scroll through all the different teams and specialists that we have because it certainly takes a village. I would say core to our go-to-market function.

We obviously have our direct sellers. We work very closely with our sales or solution engineers. So they are the technical prowess and strategy behind a lot of the projects we’re working on that we then have specialist teams that are verticalized. We have financial services, we have oil and gas energy, we have e-commerce and we’ll often pull in those folks to get multiple layers into a conversation, to ensure that we’re helping build out a broader business case. And then I would say marketing partners are huge components that we work really closely with — Google and AWS in particular. And on the marketing side, we’re always trying to do different events and workshops and things to keep our customers engaged and successful.

Tony: Oh. You know, at this point in the pandemic, I think it’s safe to say we’re all a little bit Zoomed out.

Hannah: Well, I couldn’t agree more. That’s why I love Reid’s approach to ensuring teams are communicating effectively without booking too many unnecessary meetings and touch-bases.

Tony: Exactly. I can’t stand having too many unnecessary meetings. But I think cross-functional collaboration is all about striking the right balance between working effectively as an individual and keeping communication channels open with your entire team.

Hannah: But I also love what Reid said about celebrating small wins to stay motivated. I think celebrating together as a team is a really great way to strengthen those bonds and form authentic connections.

Tony: Absolutely. And if celebrating those wins together includes a cocktail or two, then we’ll do what we have to do. But I think finding cross-functional alignment is more important than ever today as the landscape becomes increasingly competitive. So going the extra mile is always worth it.

Achieving excellence in enterprise sales

Hannah: Agreed. Let’s hear what Reid has to say next about achieving excellence in enterprise sales.

Tony: With all that in mind, do you have a specific focus for this year or is there a specific goal that you’re targeting… or how are you thinking about the upcoming fiscal year?

Reid: I guess if my manager were listening, he’d want to hear my aim is to hit our team number for the year, which certainly is a goal. But the way that I look at it, and I’m obviously newer on leadership, I try to think about it as a bit of a framework or kind of trickle-down effect to our end goal, be hitting our number. What are some of the other kinds of leading indicator goals that we need in order to get there? A big one for me is ensuring that I understand what my team’s goals are for the year. Some of them are going to be purely numbers/financially based. Others want to get into leadership or get exposure to other teams.

Making sure that I have a full understanding of what success means to them and then building that up into how we get there as a team to hit our number, that’s probably my overarching goal for the year.

Hannah: And Reid just kind of expanding on what you were saying regarding enterprise selling: one of the key differences you mentioned is there’s the inherent strategic nature of an enterprise setting, right and also the multiple stakeholders that are typically involved. What’s bringing all that together? What are some of the recent sales wins — of course, those that you’re allowed to talk about — that you are proud of? And what do you think are some of the factors that resulted in these wins? So, think of a salesperson listening, who’s thinking: What do I need to do on my next call to be like, Reid?

Reid: That’s a good question. A good win that we had that I could share happened prior to the holiday break. We were working with another data SaaS company, actually local here in Canada. They put a significant premium on security and, in turn, uptime. It wasn’t the largest from a dollar perspective but, from a complexity standpoint, it was pretty significant. So they have contracts in the US where they require steady ramp capabilities. We had unique compliance and legal components to it.

I think one of the things I’m most proud of and what’s important on the enterprise side is it was a nine to 10-month sales cycle, but we did a really good job at the beginning, building a strong relationship with multiple stakeholders — leaders at the business, technical owners — and we tried to have some of the tough conversations early on to get those out of the way. We knew it was competitive and we were going to go to an RFQ, so we tried to get ahead of where we were strong and where we may be weaker or at least what our competitor was going to be meeting on,  what did our license model look like and what would the cost look like. That way, when we got towards the end, we had had a lot of those challenging conversations — the ones that maybe come with a little bit more back and forth — and it ended up being much smoother. There were still negotiations to be had, but we had built a lot of rapport early on so that we could have those conversations easily and ultimately partner. I think it’s a big reason we won the deal.

Tony: It sounds like you did a great job and, like you said, establishing those relationships was a big part of that. And touching back a little bit to something you said earlier about getting to understand a little bit more about your internal teams: what their goals are, what sort of things they’re looking to do. As you’ve collected all this data, have you found that there are certain challenges that are bigger ones that you want to make sure that you can work through with your team? Are there any challenges that stand out to you right now?

How to build natural urgency

Reid: I think one of the biggest challenges that we come up against is just building natural urgency. I always try to get my team away from just selling to the end of a quarter or picking our own timeline or deadline, because that’s often when I find deals slip and forecasts get impacted. I also know that, as sellers, we can’t make our own agenda. To get a deal done, we have to work with our customers and understand what’s a compelling event for them. And that’s much easier said than done.

Sometimes you have to do it around product launches or sprints, and the engineering team is running around dealing with other major projects that don’t even affect you, but they open up resources for your project. I try to get my team to do a far better job of just leaning in and identifying upfront, “Hey, we want to work with your team’s timelines, but we want to pick a date and work backward from it.” That inherently is a challenge, but it’s also something we’re trying to get better at because if we can build natural urgency, then we ultimately have a time and a date that we’re working towards. And we also have a bit more leverage when it comes to getting into final contract negotiations.

How to be easy to work with

Hannah: You were speaking briefly about the challenges that you’re working on for your team. And urgency in deals… it’s a hot topic, right? It always has been. But I’m just thinking about the wider ecosystem that you work in at Splunk. You’ve been there a few years now. You went from an RSM to it to a sales director. What were some of the key differences you noticed as you made that transition? What are some of the things that stand out with how you’ve had to work with the team as an RSM compared to how you need to work with the wider ecosystem as a sales director?

Reid: As an RSM, one of your biggest focus areas needs to be ensuring that you’re working collaboratively with your sales engineer or solution engineer. Especially with a complex sale like Splunk, they’re so critical. And I think that, just like sellers, you get a wide range of personalities when it comes to sales engineers.

And so, as I always tell my team, when I was an RSM, I was going out of my way to make their lives easier. So I didn’t expect them to do meetings, follow-ups. I didn’t. If I needed a technical document that I could Google just as easily as they could, I’d go out of my way to do some of those tasks so that when I really needed to lean on them — if we needed to go after hours and really close in on a project — they were willing to do that. I find that if a rep takes the easy way out or goes lazy, they’ll get the same in return from their SE. I made a very conscious effort to make working with me as easy and enjoyable as possible. And I now try to ensure my team is doing that so that when we need help, folks are willing and open to come and work with us.

Tony: Digging into that a little bit, how do you align with your teams? Do you see it as, “Hey, this is just something I need to do one time?” Or is this part of you? It sounds like it’s part of your overall methodology with your teams but tell us a little bit more about that.

Reid: Alignment is certainly always fluid and continuous, and it changes depending on the project and customer that we’re working with. But I always try to have consistent communication and alignment across all of our cross-functional teams.

I am cautious of having too many meetings. I try not to have just meetings for the sake of them. I try to be as efficient as possible, but I count on my team to be ensuring we have that active alignment and that folks understand their roles and responsibilities from the early stages.

So, when we’re doing our first-half kickoffs, for instance, or our quarterly business reviews, if we have accountability early on around, those folks know that they’re going to be counted on, and that generally breeds a good, healthy level of alignment and responsibility.

Hannah: I’m a big believer in motivation and positive thinking and affirmations and things like that. And I think you need a lot of that in sales, right? This is the step: that one moment where something needs to help, right? Or the universal powers. But what is motivation like for you? How do you connect with and motivate the people around you, particularly the people in your team?

Reid: Yeah, that’s a good point, Hannah. One thing I learned early on and I actually was not great at was managing the highs and lows in sales. A mentor of mine talked about just not getting too high and not getting too low either. And that was a learning curve for me. I was always more of an emotional seller and I think you’re right. You need you need to have positivity in the good times and the bad. With my team, we always try to celebrate the wins, even if they’re smaller wins. So maybe we haven’t yet closed the deal but we got through a huge milestone. Or maybe we broke into just booking meetings with an account that we know is a high priority but haven’t had much work with before.

As part of our team meetings, I try to get my team to share and open up about what’s working for them. While selling can be an individual sport, at times we try to make it like an overall open landscape where people can celebrate and also where people can identify, “Hey, I’m having challenges here. Have you folks tried to do something different?”

Also, sales folks are generally pretty competitive. So if you are the top performer on your team is continuously sharing wins, it tends to bubble up to other folks.

Hannah: It really does.

Tony: Well you said, you were a hockey player earlier, so I think you got to share the wins, right? That’s all part of the team mentality with hockey. So.

Reid: Exactly.

Tony: So it’s funny. We were talking about hockey offline before, but everybody consistently says about hockey players that they go above and beyond, right? They’re not like the guys who go down with the fake injury like in other sports. So how do you how would you relate that to sales?

Reid: Yeah, I’d say there are two components of that that I’ve noticed. Number one is just if you’re willing to put in the work and work harder than the other 90 percent, you’re going to be largely successful in sales. It’s not the only telltale sign but I have found that, for the most part, if you really are hungry, you’re passionate about what you’re selling and you’re interested in what your customer’s goals are, that’s a way to stand out in itself.

One of the big things I see is just the level of preparation. So with top sellers, there’s this framework.

It’s like the principle agent framework where you want more and more of your team to think like an owner. I think the best reps treat their territories as they own that territory, right. They’re the GM or the CEO or whatever you want to call it, of that territory. And that means slowing down. Every single action is value add and putting themselves in the framework of their customers for the largest strategic deals, thinking like they’re a part of that team. Where does our solution have to fit? What challenges does it have to meet? That’s the top sellers that I see. They’re willing to go out of their way and above and beyond and to really think like an owner, and I think that’s a huge component of being successful in sales.

Hannah: So Reid, you’ve mentioned quite a few things about what you can do to improve your ability to deliver sales outcomes for your business and your customers. You mentioned things about collaborating well internally. You mentioned acting like an owner and finding positivity during the highs and lows. But what about some of the recommendations that you’d make to somebody who’s getting started in their sales career? You’ve already mentioned working at a startup, so you can’t say that one again!

Reid: Yeah, sure. That is a big one. I will say I was going to default back to that, but I’ll follow your guidance. I think finding a space that you’re passionate about is important. I think you really have to care about what you’re selling. You’re going to be doing it every single day and it can be a grind, so if you don’t necessarily believe in the space or you’re not genuinely interested in it, I think that would show on long calls, right? And in today’s world, you have to be much more of an advocate and customers just have so many different options. If you’re going to be successful, you’ve got to care about what you’re going into. And then also just picking strong, strong products in markets with lots of upside. I’ve always loved that the reason I went to Splunk was I looked at the size of the data market, data monitoring, and cyber, and I just felt that there’s so much growth opportunity. So finding markets with plenty of upside and tailwinds is important.

Hannah: I think people often overlook that. It’s a really good point. Thanks for that.

Tony: I’m sure Splunk is changing quickly. How do you go about refining your skillset right and making sure that you’re where you need to be, not only for your personal growth, but for the organization?

Reid: One of the first things I do is try to identify people who are smarter than me or have been more successful than I have, and I just ask them for guidance and to spend time. I try to be as respectful as I can about it and I come prepared, but I don’t really shy away from it.

At Splunk, one of the first things I did and I continue to do is have mentors who I try to keep up with, learning, taking their brain, kind of being a sponge, if you will, to pick up different tactics that they’re using and make them my own.

So that’s a huge component of it. And then I also am fairly active. I use tools like Twitter and a number of different blogs from other sales leaders and go-to-market groups and just try to make sure that I’m staying up to date and relevant on a lot of the trends because I find that, once something is reaching kind of LinkedIn blog velocity, it’s already being used by a lot of sellers. Trying to remain consistent and sharp on new ways and strategies folks are using has typically yielded good results so far.

Tony: Well, you’ve kind of defined my whole career: being smart enough to know I’m not the smartest person in the room. I think that we’re very much on the same page with that.

Hannah: It takes a while to be comfortable with that and realize the benefits of that actually. I know this is definitely a valid point. We’ve spoken quite a bit, indirectly, about communication when it comes to working with internal teams and when it comes to working with your sales team. What are some of the tips you have for ensuring smooth and effective communication? Because there’s a lot of ways to communicate now, like informal, formal, etc. Tell me more about some of the tips that you would recommend when it comes to comms.

Reid: Yeah, there is no shortage of communication channels these days. I really like the concept of radical candor: the idea of being openly transparent and also very direct. I find that that’s the feedback that I always hope to get and I try to embody that in my communication with my team. I find that it’s best to be very, very open and honest about performance. And if that’s to the negative side, obviously, it’s coming with constructive ways to improve on what we’re doing. And if it’s to the positive, we need to ensure we can replicate that and make it more of a playbook going forward. I guess to your point around channels, Hannah, I find that still just picking up the phone and calling is one of the best ways to really have a conversation, particularly if it’s more of a difficult one. I think Slack and email messages can sometimes be misconstrued, but there’s a time and a place for them. I also found that shift has been really different, moving from when I was in a full office. In a setting that’s been fully virtual the last two years, it’s been even more challenging at times to really connect with folks. I find there’s always a little bit of that barrier on Zoom calls and such. And so, again, meet for a coffee or get in person if you can, but if not, phone calls generally the best.

Hannah: Yeah, but Reid, emoji or no emoji?

Reid: I’m not much of an emoji guy. I’m a I “Iike” guy.

Tony: Actually, thinking about the challenges you were just mentioning. Can you think of a time when there was a communication breakdown that had a direct impact on something you were doing? Can you think of anything and how did you solve it?

Reid: I mean, there are communication breakdowns — they happen all the time. I’m even thinking how we work with customers. Sometimes emails can be misconstrued or just missed in general. And so the best way, in my view, to solve it is, if we feel like we’re going down a path or maybe there’s a disconnect, it’s just kind of hitting pause, with me putting my own hand up and saying, “Look, I think I’m missing the point or maybe I was I was unclear. Can we do like a hard reset on this and just kind of try to figure out if there is a better path forward?” And I think identifying that early, early on and not trying to pretend like we know everything or go down a path that’s not the right one. It’s probably best to nip it in the bud when you when you have risk of a miscommunication.

Hannah: I’m just thinking about something you mentioned earlier. You said you’re relatively new to leadership. I think I was doing a little bit nosing around on your LinkedIn. It’s about a year, right, since you transitioned into a sales director?

Reid: Yes. Yeah, I’m starting. We just kicked out at this level at the end of January. So this is the start of my second year.

Hannah: What are you hoping to improve? You’ve had a year of learning and probably some shocks along the way, but how are you hoping to up level your leadership skills for 2022?

Reid: There’s a long list. I’m actively trying to find ways to get better, and I’m pretty open with my team about that too. I’m in a unique situation where I joke that some of my team members have been selling since I was in high school. So they’re all far more senior than me. One thing I try to do is just take the approach of not knowing everything and being very open about, “Hey, here’s where I can help, and here’s where I where I want to get feedback.” Something I think I can do more of is press for more critical feedback. I find sometimes asking for feedback can be really difficult, and sometimes folks, particularly if you have a friendly relationship, will take the easy way out. They’ll say, “You’re doing a great job, thanks so much.” But that’s rarely the case. There are always going to be areas that I can improve on a one-on-one basis, but I also want feedback about how I manage teams. And I’m not going to let them off the hook when I do ask for feedback because it’s really the only way I’ll improve. So that’s the main focus of mine, among others.

Tony: You said you’re about two weeks into your new fiscal, right? What’s next for you and for Splunk over the next year?

Reid: So Splunk’s going through a pretty big transformation. I think we’re one of the largest companies, aside from Adobe and Autodesk, to move from a more traditional on-prem software to being fully cloud native and SaaS. And so that’s come with some growing pains over the past two years, but it’s also been really unique to be a part of. What’s next for us is just really ensuring that we’re laser tight on just what being a SaaS company means. What are the critical metrics I mentioned that touched on whether we have organic growth? How do we land new deals? How do we ensure we have retention and renewal? So that’s a huge focus area: best practices around being SaaS company now. And for my team, it’s a matter of ensuring that we are educating our customers about those changes and ensuring that they’re aware of all the different things that Splunk can do. We’ve always said it’s a blessing and a curse, where we are very good at a lot of different areas, but we often will get stuck in one segment. So jumping over to other buying centers, whether you’re in security or moving into IT, can be challenging because the folks that own Splunk tend to hug it and keep it very close. Having the opportunity to build and grow and expand teams can be tricky, but it’s needed if we’re going to kind of continue growing at the rate we are.

Tony: Oh, that’s great. Well, Reid, this has been fantastic, but we’re not done with you yet. We have just a couple more questions that we’re going to do in our rapid-fire round. Hannah’s going to kick it off. Give really quick answers: the first thing that comes to mind.

Sales podcast rapid fire quesitons

Hannah: All right. Let’s get into it. So, OK, what is your sales philosophy in just three words?

Reid: Always be interested.

Hannah: I like it. What’s the best advice you’ve been given in your career so far?

Reid: Find good mentors.

Tony: I like that one. Your top productivity hack?

Reid: Own your calendar. I’m a huge fan of blocking anything and everything I need to get done throughout my days.

Tony: Very smart. Top prediction for the sales industry in the upcoming year?

Reid: Product-led growth is going to continue to flourish so reps need to find ways to be effective and change their models in some cases.

Hannah: What’s one thing that you believe is revolutionizing the sales industry?

Reid: It’s probably the amount of tools and resources and, in some cases, cutting through the noise of what are effective tools and how to help reps work as efficiently as possible. I think the efficiency and productivity metric is just going to become more and more important, particularly for teams, when they’re justifying raising new rounds or where they’re allocating dollars for headcount. It’s a huge component and probably will be more and more.

Hannah: I think I’m with you on that one. But on rep productivity, if you could share just one piece of advice to salespeople, what would it be?

Reid: Always be authentic and transparent.  Be as open as you possibly can and then try to be somebody that a buyer likes to do business with. There are so many tools and options out there. People still like doing business with folks who they find enjoyable and whom they see they get value from.

Tony: There are a lot of voices out there nowadays with blogs and posts and everything. So where do you go to for your best sales industry news?

Reid: I’m a huge Twitter fan. I try to use Twitter and be selective of my followers, but also make sure that I’m staying up to speed. I like a few different podcasts, and then I also try to read more books. There are a lot of good books out there.

Hannah: OK, so are leaders made or born?

Reid: Both. I don’t know. I don’t think one versus the other.

Hannah: You’re allowed.

Tony: You can. You can.

Hannah: You’re allowed.

Tony: Well, this is our last question. I’m actually a big movie fan myself, so we’re going to tie this to movie quotes. But would you go with always be closing or sell me this pen?

Reid: Always be closing.

Tony: I knew you were going to say that because you gave us a couple of these already, so I had a good feeling that you are going to go that direction. But, Reid, this was a fantastic time today. We really appreciate you joining us on Ready Set Sell and we wish you the best of luck at Splunk. Thanks again for your time.

Reid: Awesome. Thank you so much, Hannah and Tony. I really appreciate it.

What we learned

Tony: You know, I thought it was really interesting with all of the different roles that Reid has had over the years, because that’s pretty consistent with what I’ve seen from a number of top sales leaders: they’ve done different things and they have unique perspectives because they’ve really been able to see things from different lenses within the sales verticals. I think that gives him a great way of being able to really visualize from a different perspective.

Hannah: I definitely agree with that. I think it even goes beyond having experience at various levels in sales. I think the sales leaders that really exceed expectations are the ones who have actually had the good, the bad, and the ugly parts of sales experience. So they’ve had incredible years but maybe they’ve had a quarter where they haven’t done so great. And the reason I mention that is that they are able to really think about, you know, how will my team be feeling right now when they’re doing great? Or how will my team be feeling when right in this instance when they haven’t hit a target? And I think when you’ve got leaders who have gone through various different roles in sales, full stop, they they’re much more relatable when they can relate to the different situations that salespeople find themselves in.

Tony: Yeah, I think it really gives you a lot of credibility as you start rising the chain. I mean, I look at my background. My first job out of college, I was selling sneakers. You know, I was the top sneaker salesman in northern New Jersey, which brought me to where I am today, I suppose. But it really gives you an idea of how to think about things differently, because even though I was selling sneakers, I learned a lot about how to deal with people and different dynamics with the people I was working with. I think every job that you go through or every stop on your way really helps define who you’re going to be and how you’re going to work with colleagues within different structures.

Hannah: Yeah, I love the sneakers. This is great. When you think about the roles that all of us had and you think about the importance of coaching now, as a sales leader, how can you coach if you haven’t done the job yourself? Or how can you really effectively coach if you just haven’t been in the trenches, the multiple roles that you play and the experience that you gather from that? I just think it sets you up to be a much stronger coach, which, in my opinion, is a key part of being in sales leadership.

Tony: Yeah, absolutely. I think that all adds to credibility, right? And we’ve all had managers over the years that, you know, get put into positions of leadership and have not done the job that they’re asking you to do. And they don’t really get the credibility because they haven’t done it and they’re asking you to do things that either they don’t know how to do or just haven’t had any experience doing. I totally agree. I think it’s very important to have someone in that role that can not only talk the talk but walk the walk. Reid’s clear and articulate understanding of his role in the team really impressed me.

Hannah: I know, right? Like, it became quite clear early on in the interview why he’s moved up the ladder to a leadership position.

Tony: I know he really had some great suggestions to share about finding cross-functional alignment internally, managing teams effectively and really going above and beyond to achieve excellence in sales.

Hannah: I think one point he made that really stood out to me was the value of finding someone who’s more successful or experienced than you and learning as much as you can from them.

Tony: You know what they say? It’s funny. I use this too. If you’re the smartest person in the room, you’re in the wrong room. I think Reid also emphasized the importance of following your passion in sales. You know, I couldn’t agree more with this point because if you’re not passionate about what you’re selling, people will be able to sense that and you’ll see it reflected in your results.

Hannah: It’s true. And finally, Reid’s comments about accountability and responsibility were so on point. Getting clear on everyone’s roles and responsibilities from the very beginning will help set everyone up for success and lead to stronger alignment overall.

Tony: You know, absolutely. I think, all in all, I learned a lot from today’s episode, and we hope that you did, too. Thanks again to our guest Reid for joining us today.

Hannah: Thank you for listening to this episode of Ready Set Sell.

Tony: We hope you took away some valuable lessons and insights that inspire you to reevaluate your approach to sales readiness.

Hannah: Don’t forget to subscribe, rate and review the show when you get a minute.

Tony: And stay tuned for the next episode of Ready Set Sell.

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