How to Survive and Succeed in High-Pressure SaaS Companies

Welcome to the Switchgear Show. This is your host, Preet Sarkar, and today we're joined by Jeremy Orbach. Jeremy, welcome to the show.

Thank you, Preet. Thank you for having me.

I've known Jeremy for a number of years and he is an absolute top-performing account executive, and he has worked with some incredible companies like Salesforce, MuleSoft, and UiPath through their growth and scale-up journeys. And he has basically top-graded and achieved Club. So I've invited him to really just get into the conversation of going through the highs and lows and the stages and what he's learned and to share with us. And I think it's going to be a fantastic conversation. So again, very excited to have you here.

Thank you, Priyank. Looking forward to the chat.

All right, let's jump right in and tell me, how did you get into sales?

Great question. If we go back a lifetime ago, now I actually left university as a qualified surveyor. So I actually started my sales career actually selling large commercial buildings in London. That's really how I got into sales. But the GFC hit. It was a terrible time, both in real estate finance and in London, quite frankly. So I needed a bit of a sea change, came out to Australia. Nice. Pretty much just to take advantage of the lifestyle, have a bit of a break and see where kind of life took me. And I was very lucky actually to land a sales role with a really small Australian communications startup that was selling some subscription software. So that was really my first taste of subscription sales. I was hooked, I loved it. And as time went along over those 6 months, I was able to build a network and really get my feet under the table, but I had one big problem and And that was that they couldn't sponsor me to stay.

Ah.

So at that time, there were only really 2 routes to getting into Australia on the visa program. That was actually one as a recruitment consultant. Obviously being English, I think you probably actually know a lot of people go down that route. And the other was tech sales. So as my visa started running out, I was looking harder and harder for jobs, but it got to the point where actually I didn't have any offers and I was effectively deported. So I actually said back to the UK because I started to build up a network, friends, that lifestyle, you know how it is. It's great living out here. But I was fortunate that I had started some interviews and after some very late nights and lots of conversations and the help of some friends, I got 2 offers. One was with Robert Walters to be a recruitment consultant.

Yes.

And the other actually was to be a BDR with Salesforce. And at that time Salesforce were pretty small still in the market, although I was a bit apprehensive actually about taking the BDR role. I thought, It was a bit too junior for me, but I was completely wrong about that and took the Salesforce gig, flew straight back out and I really never looked back. And that was about 11 years ago now. So it's been a bit of a journey since then.

Oh, wow. That's a great story.

That is a good story. You know, it was interesting. It taught me a couple of things. It taught me that networks are obviously vital because without having a couple of friends already working at Salesforce, there was absolutely no way I I would've got that offer. But also, I took a step back or a perceived step back in my career, but it actually led to some really accelerated personal and professional growth. And that was a really key learning for me that I've kept close to my heart ever since then.

That's terrific. Look, and I think that I see patterns of success and patterns of failure in the work that I do on a daily basis. And I just think that people who are able to move continents or countries and reestablish themselves. I just see a pattern. There is a— we just see people who do really well with that. As well as you obviously navigated a situation and took a role as a BDR. And that's another role where we've seen some very good AEs come out of BDR intakes a long time back because you just develop really good discipline and then use that for the rest of your life.

Couldn't agree more. Some amazing foundational skills, really is. And it's topical at the moment, isn't it? There's a lot of talk around SDRs and BDRs probably being the hardest job in sales at the moment. You do get an absolutely great understanding and it sets you up for success. Absolutely.

So now tell me, you've chosen scale-up companies as you've grown in your career. Why do you work for scale-up companies?

Oh, good question. To me, it's twofold. Scale-ups often offer a product or a solution where they can solve some key challenges and there are gaps in the market, and they're often moving a bit more quicker and a bit more agile than the larger players. So they're offering something that has some real tangible value, and that creates opportunity, opportunity both for myself and for the customer. And then the other side as well, it's a personal opportunity.

Mm-hmm.

Scale-ups come with a lot of challenges and there's a lot of challenges to overcome. And it's often that journey of those challenges that excites me often more than potentially selling a deal because you've got to get to that deal. And whether it's lack of resources, working out what your go-to-market is, building up the brand awareness, those challenges are incredibly exciting. And it's interesting, I was listening to a podcast last week and Justin Borgman, he's the CEO of a great startup called Starburst. He's, I think he summed up really well. He said, if you wanna work in a scale-up, you've gotta be what he terms an owner. And that is somebody with the ability to wear many hats and collaborate across all the different teams within an organization. And that summed it up really nicely for me. That's what I love to do and I've got a passion for it and it excites me. So that's why I tend to go towards those companies.

Yeah, no, and I think my personal observation is that people who are clear about what they want are far more likely to get it, number one. And people who are clear about what they don't want are also far more likely to avoid situations where they're just not a good fit. I think clarity is a superpower. That's really something that I believe in. Now, I know that working in scale-ups can be a rollercoaster ride where there's a lot of hopium around what should, would, could happen. And sometimes things keep moving quarter by quarter. So, tell me, how do you succeed? If we were looking for a formula or a framework, how do you end up succeeding and staying in scale-ups, especially when the narrative is not playing out the way you think it should?

Oh, wow. I do have a framework, but I'll say this now. If you've got any listeners that like dogs, they probably won't like this framework. So, just bear with me. To really be successful, You've got to act like a cat. Now, I tell people this and they often laugh at me, but let me spell it out for you. Cats are inherently curious creatures, okay?

Hmm.

So, if you take the C of CATS, you've got to be really curious. And I don't mean just be curious about the product you're selling. I'm talking about everything, curious about the products, the solutions, the people you're working with, the customers you're selling into, the verticals you're selling, because that curiosity is going to give you the foundation succeed within that organization.

Hmm.

If you take A, what does A stand for? That's acumen, really having some business acumen. You've got to have business acumen to overcome the challenges, both to educate the market, but also understand where your solution product fits into the macro and microeconomic conditions that are happening within that vertical. And the T is for tenacity. So, everyone knows sales is hard. It doesn't matter what job you're doing in sales, it's hard. But in a scale-up and also a startup, it can be especially hard. So you've really got to have that mental fortitude to overcome some of those challenges, keep your eye on the prize, and then drive forward with that growth. I've got a good story for you in terms of how that framework can play out if you want to hear it.

Yeah, I'd love to.

So the first, one of the first, it was the first C-level meeting I got at UiPath was with the CIO of one of Australia's largest healthcare providers. We'd done the normal thing, it had taken a while to get to him. We thought we'd proven out the solution with the people reporting into him. We'd done a lot of planning, turned up to the meeting. After some pleasantries and a bit of chitchat, probably lasted 3 minutes, maybe not even 3 minutes, where he turned around and he said, I don't think this solution has absolutely any relevance for us or for healthcare. I'm going to ask you to leave. And he literally threw us out of the room. To this day, by far the worst C-level meeting I've ever had. I walked out, it was a real, it was a real kick in the guts. Like, I mean, weeks and months of work to get there. And what do you do in that scenario? Do you just let it go and go after other customers? No, I wanted to be like a cat. And I used this framework to go back in and be even more curious around what really was it that we could really bring to the table for a healthcare provider. So, I spoke both internally to Quidiz, externally, globally, even spoke to other healthcare providers using UiPath around the world. And came up with a couple of use cases that I knew they were struggling with for the macro environment reasons that they were going through in Australia. Used my tenacity to go back and do some multithreading at another part of the business and really get up towards the CFO. And we finally got towards the CFO after about another 3 months, presented these use cases, which he loved, sponsored a pilot, which went well. And if we wind forward, I think, 4 or 5 years now, they have their own in-house automation team and things are going pretty well for them. So I genuinely believe that kind of framework, acting like a cat, can really make you succeed within these scaled-up companies.

That's an amazing story. That is so good. And especially when I think that most reps, after being asked to leave by the CIO, seeing that there was no chance, would have just potentially started prospecting in other accounts. But the fact that you cross-reference other use cases with healthcare around the world, and you started being curious and finding opportunities right through up to the office of the CFO, that's amazing.

I just, it made me angry, if I'm honest with you, more than anything. Most people know it takes a lot to get a C-level meeting. When you do, you want to be prepared for it. And most people you meet are really open by the time you get there to have a very open conversation. with you. So I think it was more that anger more than anything that kind of drove me on to really want to succeed within that account.

That's amazing. That's great.

Wow.

That's a good one. That's really good. So in terms of navigating those situations, tell me a little bit more about any sales methodology or core principles that have helped you continue to exceed quota, make club, What is it?

Yeah, to me there's a couple of things. Sales methodology, absolutely incredibly important, I think, especially today more so than ever. Now there are lots of sales methodologies and they fit different scenarios and different solutions. They've got to underpin your sales process and your go-to-market. Now if we look at today, just divulging a bit, but the average number of stakeholders to close an enterprise deal has ballooned to about 15 people. Okay, 6 a few years ago. So how do you effectively sell to 15 people if you don't use some kind of sales methodology? To me, sales methodology gives you the operating rhythm you need to succeed, and it creates the same common language that the whole team can work towards to really underpin going after some of those larger strategic deals. Now, in combination with that, just, just on myself, I follow some of the principles of Dale Carnegie.

Okay.

Book, How to Win Friends and Influence People, nearly 100 years ago. But to me, people still buy from people. And some of the key principles around listening, communication, and really being interested in people has really served well with that kind of mixture of sales methodologies. You can start to build out your stakeholder maps and your opportunity plans.

Wow. Yeah, absolutely. And I think that I can say this as a recruiter who is involved with over 100 startups, scale-ups, and some of the best-known tech companies in the industry, it's about people at every stage, at every scale, from executive hires to client relationships to mobility and transition to funding. It's all about people. So, I think that's really good. Tell me some of the biggest challenges that you've had to encounter along the way.

Another really good question. When I think about it and kind of look back over the last decade or so, I think there's 3 main challenges. And I'm probably looking more from an IC perspective than anything else around how to succeed. First is brand awareness. Salesforce, even Salesforce originally, back in the day, it was only known for CRM. So when it started to expand and bring on more, more and more products and solutions, again, it was brand awareness. And that's a real team effort. You can't just rely on marketing, potentially with a small budget, to go and do that. So that brand awareness is really key to start educating the market and starting to grow your customer base as quickly as you can. Time management might sound a bit silly, but as an IC, you are still employed to set. You've got to hit a target, and often there's so much going on within the scale-up that you can potentially lose sight of that. But you've got to remember, there's only a number of hours in the day where you can speak to customers and prospects. Your time management is absolutely key. And I think thirdly is the noise. So scale-ups create— can often create so much buzz and so much excitement. There's so many different things going on, whether that's local events, sales enablement, change of Change of strategy, different management coming in, new people coming in all the time. There's a lot to distill, but you've still got to remember you need certain things to help you do your job effectively. So you've got to distill that noise, work out what can really help you, and then use those assets and resources to go and succeed. So it's really those 3 things: brand awareness, time management, and cutting out the noise.

And how do you Overcome those and then set up a year where you are smashing quarter and achieving club.

Yeah, I've often thought about this. I think it's it's a really interesting question. Achieving club is the really is the pinnacle achievement for an IC. It shows that you are succeeding often with shrinking territories and increased targets. What I try and do and find interesting is actually I look to try and achieve club. Almost in the latter years of tenure. That might sound a bit silly, but if you hear me out, there's often in the first year, it's often about new logo acquisition, really trying to get into your territory and understand who you're selling to, why you're selling to them, what's working well. And if you can open the door successfully, then it's about trying to cross-sell and upsell and getting those larger deals. So if you're hitting club in your second and third and fourth year, it shows me that you're growing your customer base, your average deal size, and you're often always competing against harder competition. So it's really setting yourself up for success every year and understanding who you're selling to and why you're selling to them.

Yeah. Wow. And along the way, how do you manage the smaller deals versus the large enterprise deals? Right. So how do you architect the big wins whilst ensuring that you keep the smaller ones moving, ticking along?

It's a tough one. Yeah. You do need that run rate while you're going after the larger deals. It's tough. I haven't met anyone yet that I suppose can give me the golden answer to that question, quite frankly. For me, it actually comes down to a lot of that sales methodology. You have a couple of key bets throughout the year, absolutely. And if you work out your— to be honest with you, I use Mitterheimer. I use Mitterheimer for my large strategic deals because Mitterheimer gives you the basis to really understand your stakeholders. If you've got 15 or so stakeholders, you need to understand their personas, what's driving them, what are their challenges, their priorities, and you need the methodology to actually go and take that forward over a certain amount of stages, so you're in a position to make a proposal and potentially have a deal. That's a long process. Large deals can often take a while, so you've got to have the patience and collaboration to do that while keeping your eye on the ball with some of the smaller deals, more transactional. To me, it comes down to more time management and that curiosity again. If you've got the time management, then you've got enough time to do anything. And as long as you're continuously curious and always building up your knowledge base, you will be in a position to do those larger deals.

Yeah. Wow.

I don't know, Priya, if anyone's given you the answer to that golden answer, how do you keep the run rate going and go after larger deals? Love to know the answer really, if there's a silver bullet to it.

Yeah, I think that you've talked about Curiosity, acumen, and tenacity. I think there's an acumen, that component in between, which is like an account to which you make more deposits every time you win deals and every time you lose deals. So you're taking— sometimes you win and sometimes you learn, and that builds that base of acumen as you go along. I remember life before my first club and after, and just my ability to plan my— the months, the deals, and really get a sense of I'm going to have X amount of deals to be able to do this. Just there was an acumen and an understanding that did not exist before, which then helped me pace myself month in, month out in terms of what I needed to put in to at least get the level of pipeline that gave me a realistic shot. Because I like how I felt being referred to as someone who made club. And I liked what the account looked like as well. It was a win, right?

You want that experience. You can't discount that experience, can you? Not just in club, but it's not even club. Once you've done your first big deal as well, understanding how you did it and the potential pitfalls that could have stopped you, that, yeah, that absolutely feeds into that knowledge to do it again and again.

Yeah. Tell me, in terms of advice to your younger self, Or to someone who's 5 to 10 years, people who are absolutely killing it in commercial and mid-market and looking to get into enterprise at some point of time. So what are some of the mistakes you've made and some of the learnings that you're taking away from that phase?

Great question. When I was in, even in SMB and commercial, I was always told selling into enterprise is a whole kind of different In reality, it is and it isn't. There's just, there's a lot more people to sell to. There's more politics involved in it. You might have to have some more direct and pointed conversations, but the skills that you would learn, and I tell myself if I was to go back, that I was learning in SMB and commercial, absolutely stood me in brilliant steps to go and do really well in enterprise. Because you just, if you think about a commercial deal and there might be one or two stakeholders involved in it, you've got to expand that to, you know, Maybe 15 people, you're still doing those same kind of steps with those 1 or 2 people. You're still potentially qualifying the same, still following similar methodology, but you just got to expand it. So I would say to those that say there's a vast difference, there is and there isn't, but you've still got a very good foundation to go into enterprise. Some of the big mistakes I did though, and even today sometimes I still do them, happy years. Now, Everyone talks about happy as though it's almost like a junior mistake, but it's not necessarily. In scale-ups, if you're bringing out a product or a solution, a lot of people are interested to understand what you're doing. That doesn't mean though that they're in a position to buy or even want to buy from you. So you've got to get through that noise and you've got to qualify properly. So qualifying, I can honestly say in my early days in both, all of them, Salesforce, MuleSoft, and UiPath, my qualifying wasn't good enough. So, that was a big mistake and a big learning. Qualifying out is almost important as qualifying in. So, it gives you the time to work with the customers that are actually interested in buying the product for you. Assumptions too. I would often in my early days make assumptions around how a meeting was going to go or what was going to happen at the end of the day in a deal. And it would sometimes cloud my judgment. And so, I learned quickly actually that keeping an open mind going into any conversation, Really gives you some clarity around your judgment as that conversation goes along. So you can make the appropriate decisions there and then. So it's really qualifying, don't be assumptive, and also believe in yourself that you've got the right skill set to go and deliver.

Yeah, that's really good. That's really good advice. You talked about believing yourself, and I think that There is both at an individual level, and then there's at an organizational or a team level, which infuses itself in sales culture. You just have some— you can see it in the sports environment a lot more. When you've got clubs that win and keep winning, they have a winning culture that they build. So tell me a little bit more about really good sales culture and how critical that is to lift performance of people. What are your thoughts on that?

It's absolutely vital. It's, it might be the most important aspect of whether someone is successful or not. There's a reason in any interview I've either taken or given that somebody always asks, tell me about the culture. What's the culture? People want to know that their personality and values fit within that culture because it makes them happier, more productive, and more successful. So I think it's absolutely important. There's a small kind of framework that I use. if I'm looking at joining a company or trying to create the culture within my team itself.

Yeah.

It's called the MASS framework. M is for mindset. So, what is the actual mindset of that organization? That includes what's the mission, what are the goals, and are the people aligned around that mindset? Is everyone thinking along the same page? Do we have the right ability within the team? Hiring is obviously so important. Now, hiring isn't just for skills necessarily. It's also about personality and values. To ensure that the culture you're either trying to create or have can be sustained or built. It's absolutely vital. Structure. Do we have the right structure in place to allow people the freedom they need to go and not only succeed, but also fail, so we can always build up and learn from our failings and increase that culture from that standpoint too? And then lastly, and it's often overlooked, do we have the right systems in place, or are the right systems in place to join something? Now, it might sound really silly, but if the company's got old, archaic systems and you're spending more time trying to work out how to do things internally than spending time with customers and prospects, that can absolutely drag down the culture. It doesn't make you a winning sales culture, so that system piece is really important. It should be easy to work internally, therefore customers can find it easy to work with you moving forward too. So, that MASS framework is something that I'd look at. And I try and breathe into my teams as well. So it's vital, absolutely vital.

Yeah, that's— I can see it time after time when you have successful salespeople, they tend to come out of teams where success, people rowing in the same direction, people sharing similar values. And I can think of at least 3 to 5 of the top 20 cloud companies that I've worked with where that's happening and it's working. And then, in contrast, when you look at companies that were great once upon a time and are no longer in that season, where things are crumbling, or you could start seeing that the individual's agenda is overriding what the culture is, and you've got strong personalities driving it, which is not the case elsewhere. And you can clearly see that sales culture is starting to head for the bin.

And— It's hard to get back as well once it's gone, you know, and potentially people start talking about it outside the organization. It's hard to turn around and bring back to winning mentalities. That's why it's so vital to, if you've got it and you're building it, you've got to maintain it.

Yeah, yeah. Again, thank you so much. I think that you've given a lot today. I think that the frameworks were terrific. I think that also using frameworks to think about which kind of companies do you want to work with and whether they have a culture where you are going to be able to succeed is as important. You can succeed without it, but you are so much more likely to succeed and see other people succeed with it that I just think that's such good advice for someone who's listening to this today. So— Thank you. Jeremy, thank you so much.