Episode 17: Jason Rushforth

Episode 17: Jason Rushforth Featured Image

How do the grit and work ethic of today’s sales professionals compare to those of previous generations? In this episode of ’73 and Sunny,’ we sit down with Jason Rushforth, a seasoned sales leader with over 25 years of experience at major companies like Salesforce and Oracle. Jason shares his insights on navigating the complexities of the sales industry, mentoring the new generation entering the workforce, and the role of personal connections in career development. As his own daughter steps into the world of software sales, Jason reflects on the challenges and opportunities young professionals face today, from securing their first job to dealing with the daunting realities of housing markets and living costs. Tune in for a deep dive into the evolution of sales tactics and how enduring principles like hard work and perseverance remain key to success.




Damien: Hello, and welcome to 73 and Sunny, the podcast about the journey of getting things just right. We talk to tech sales and marketing leaders about how they’re growing, dialing in best practices and getting closer to that sweet spot. Today, I am super excited to have Jason Rushforth join us. Jason has been a sales leader for.

The better part of 25 years and has led teams in some of the largest and well known companies, including Salesforce, Oracle, and others. Jason, thanks. Thanks so much for joining us today. 

Jason: Thanks, Damien. It’s so great to be here and good to see your pretty face today. 

Damien: Thank you. It’s good to see you as well.

Let’s get personal first. It’s graduation season, right? It’s June. It’s graduation season. And I know that you just had. One of one of your kids graduate from college. So congratulations on that. I have another, I have one Michael, who is also graduating this year as well from college.

So yeah, I just wanted to first get your thoughts on, Hey, listen, now you’re a father of a college grad. So you’re a father of someone now that’s going to be in the workplace. What are some of your thoughts in terms of this newer generation in terms of career opportunities and what they’re seeing and what they’re faced with, as well as being able to afford and live and possibly buy a house.

Where you are, or I know that you’re in a nice area out in near Toronto, help, what are your thoughts on, on your daughter graduating and what’s going to be ahead for her? 

Jason: Yeah it’s an interesting topic. And, I can say that I’m pretty blessed that my daughter had decided sometime ago that she wanted to go into software and she wanted to go into software sales, which means there’s avenues in the inroads that.

Her father can help her with to obtain her first job, and through the process, it was quite interesting. She went through an interview process with one of the biggest software companies. On planet earth and at the end of it, they said you just didn’t have the experience. She’s got a degree, she’s bilingual she offers good work ethic, but she didn’t have software experience.

She worked at a golf course to pay for her school and I’m super proud of the fact that she made enough money that she could pay. But then it begs the question, right? How do you get a job when you don’t have experience? And how do you break into the market? And, I helped her focus on a couple of other opportunities.

She ended up getting a job. In the software business as a BDR and today is her second day in the office, her first her first week on the job and it’s been spectacular for her, but, a lot of my friends don’t have the same experience, depends on the profession, the career the inroads that one would have, because at the end of the day, the reality of the world we live in is your connections absolutely Can help propel your career or not.

And that’s something that, is, I was really lucky that she wanted to go into a profession that obviously I’ve spent 25 years of my life in, and but she’s worried. She’s worried about the cost of housing, when You look at the massive increase. My first home was like 175 grand, right?

That same townhouse in the greater Toronto area is selling for a million dollars. So how do you come out of school, obtain a job, start paying for the things that you have to pay for as an adult, like your automobile your insurance, your cell phone, Be able to save money to afford a million dollar dwelling.

And, it’s definitely something that worries me as a father. I’m a father of four, as I know you have several kids as well. Yeah, I know. And yeah, it, it worries me and, my, my twin daughters are just done their first year university in the United States. They play hockey.

My advice to them is, try and find a cheaper place to live than where we live today, because if you can find a job in lower cost areas, then you can, potentially afford to purchase a house and, take the traditional path that I think you and I took Damien, when you meet your wife, you get married, you buy a house, you have your kids and it’s been like that for hundreds of years and now we’re sitting in a place where, are kids going to live with us, in an apartment in the house or, How do you help them?

We’re probably forced to help them, but yeah, definitely something that’s on my mind. 

Damien: I cannot agree more with that because I’m literally in the exact same spot. So we have our son who’s graduating with a communications degree as well. He has voiced that he wants to get into software as well. And it is about the connections and it is all about, Hey, if you’re in a big.

Tech sector like Toronto, or, I’m in the Bay area to be able to have some of those connections, to be able to say, Hey, I can help you get this job. Is a huge piece of it, but at the same time, SDR or BDR salaries are not going to be able to keep up with a, Oh, a million dollar purchase.

And probably, tough with the fancy. So I don’t know. I do think that it’s the. The connections piece, the LinkedIn and just having, people brush up and getting any of that type of experience is going to be super helpful to to any of the kids. And you had said she has a good work ethic.

And I know that there’s been a lot of talk recently, I guess from the older generations, you have the whole boomer versus, Gen Z or millennials or whatever it might be, it’s Oh, they’re not working hard and. There’s the work ethic piece, but I know that you’ve worked with a lot of teams.

You’ve managed a lot of teams and lead teams of account executives, account managers, SDRs, BDRs, what’s your experience with that? Is there a gap in terms of the work ethic or in terms of what everyone’s now calling grit? Like it’s just, do they have the grit to pound the phone, to be able to get through a day of making a hundred calls and getting no in 99 percent of them?

Jason: It’s an interesting question and timely because one of the account executives at a software company who had tried to sell to me, but I thought was a fabulous salesperson posted something today about the top 10. Commercial AE and his company and he said I was in San Francisco for one week working in the office I came to work early every day and this individual was there before me every day I left the office late every day and this individual was still at their desk grinding it out and I think That characteristic still reigns true today that the top performers are always on and in driving and have that grit.

It is a gritty industry. There’s no question about it in my mind, right? It’s not a, it’s not a lap of luxury industry where you can, show up from nine to five. And I was just talking to my wife about this and she’s you can’t ask our daughter to work so, 17, 18 hours a day. So I’m not.

I said, but if she works one hour more per day, that has a significant impact on the potential performance and outcomes in her job. And as a sales leader, you have to try and flush that out in the interview process, right? If that’s what you’re looking for it’s important that you ask the questions to understand.

That if that’s a characteristic, not every sales leader looks for that characteristic. I do because I work, I’m seen at hours, right? I’m starting work at 4, 4 30 in the morning and there’s a quarter end, you’re out until midnight the same day. And in order to succeed, sometimes. Having that grit really makes an impact and a difference.

And I think as a leader, you have to decide if that’s an important characteristic, then you have to interview for that quality. 

Damien: And so what, and you wrote this earlier in a in a LinkedIn post that activity times effectiveness equals sales success, right? And so what you’re saying is that doesn’t matter if you’re the, the more experienced generation or the new generation, if you’re putting the hard work in which a lot of people are doing, then you’re going to win regardless of where, how you came in.

Is that fair? 

Jason: Absolutely. And, Damien, we worked at a company together many years ago and we used to publish report cards internally. And that report card stands true to today and any company I’ve ever been to, where, An individual contributor’s activity, which can be measured and monitored, whether you’re using GONG or whether you’re using Salesforce or any other CRM product, and you can always equate top performers to high volume of activity.

And when you talk to them, there’s a high amount of exceptional interactions. And when you put those two things together, you get amazing outcomes and results. Those are performers that are not 1 percent above budget or plan or quota. They’re 100%, 200%, 300 percent of their number. And, a lot of people will subtract the activity part.

They’ll have great experience with how they provide value to their prospects, and they’ll get to their number, and that’s okay. There’s nothing wrong. We want reps that get to drive to their number. But when you put that extra effort in, that’s when things get materially different. 

Damien: Yeah. And I love the phrase hard work beats talent.

Like you could have the most talented person that, they can talk, very well and they can convince people of different things. But if they’re not a hard worker, it’s, they’re not going to be that over producer. And it also gets into the, everyone is always saying, Oh, sales is a combination of art and science.

And I’m of the opinion. Yeah. That the science or the math is at the top of the funnel to your point where hey, it’s science It is just math if you do the work at the top of the funnel if you’re making the volume of calls The volume of emails the volume of linkedin connections and all the different things Texting and everything that you need to do at the top the that is the only way that you will get down to the bottom of the funnel Which is where really the art is where now you have these Polished, gems.

And now you’re going to say, okay, now I’m going to be able to get these as customers, 

Jason: a hundred percent, Damien, you’re a hundred percent correct, right? The, you’re not looking at the science. Maybe as a sales leader, you’re looking at the science of a total pipeline across different regions, across different segments that you sell to.

But when you get down into the art is the fun part. The science is that. Is the absolute grind. I don’t, I almost swore it, the science is the grind. It’s the, I know my ICP. I know the messaging. I know that in my territory, there’s 3, 000 or two accounts that I need to go after and I’ve got to grind it out.

And once you get them into play, the art is the fun part. That’s where you can disrupt a deal. You can be creative, you can use a lot of different tools to really drive outcomes for the business. And, that’s, I think why we talk about the art of the possible, right? It’s not the science of the possible, it’s the art of the possible because, you want to be able to showcase how you can solve a customer or prospects problems.

Damien: Yeah. And I think that, that might be what you were referring to when people are talking about. Having experience because the experience I don’t think is just on the number side because anyone can make a hundred calls a day. Anyone can do that, but do they have the experience of getting 99 no’s and one yes, and be able to have the art to be able to get that next call or to get that proposal or to get that.

That that piece. It is, it’s an age old question and I agree it’s a gritty business. I can’t believe our kids would want to to join us in this, 

Jason: but 

Damien: it is gritty for sure, for right. So you have a lot of experience in both the largest organizations and several other organizations. So yeah.

For our listeners, for either people who have a lot of experience or who are actually just joining the the sales ranks more recently what’s some of your advice for someone who is looking at, a new job and they’re looking at I, I have some opportunities at large organizations.

I have some opportunities at small organizations. What would you tell some of those people? 

Jason: Oh, it’s, that’s a loaded question with a lot of different answers to it. I did naturally advise my daughter to go after one of the biggest companies in the business. And I asked myself afterwards why, and I had a perception and then I had to step back from my perception and think about reality.

And my perception was, Hey, you can get in early. You can work with them. They have a massive sales force. No pun intended. They have plethora of opportunities to grow your career and quickly pivot from BDR to sales rep because the size of that selling organization. Inside of that, it’s, and when I worked at this particular company, it’s cutthroat and the BD, they had to set parameters.

So the BDRs were working 20 hours a day and shut off their access because they know it, you go back to the science part of the conversation and I thought to myself after she interviewed them I think there’s probably. Mid sized companies that can give you great onboarding and enablement, which is critical in a new person joining an organization that can set you up for success and still give you that career opportunity.

To grow into a software salesperson or an SC or into marketing wherever you want to go. And so my typical advice is this, right? Big organizations, it’s hard to get recognized, right? It’s a small fish in a big pond, especially with entry level positions, which means you have to go above and beyond and really stand out to get that recognition to move to the next level.

And I know that’s a generalism. There’s people on this call that are probably saying I disagree with that, but that’s the reality. If you’re on a team of VDRs, and there’s 85 VDRs on your team, you have to be a top three. Top four, top five performer against 85. Your competition pool is much stiffer. And then you have to hope you get a good territory, right?

You end up with Northern British Columbia where there’s forestry companies and mining companies. You might not have the same outcomes as a person who has Manhattan as an example. I look at every opportunity as a unique and distinct opportunity for an individual to evaluate their ability, no matter what position you are in sales, you have to evaluate, can I succeed at this particular company and that should formulate the questions you’re asking through the interview process, right?

You have to understand there’s a path that can take you from BDR, SDR to sales rep and beyond. And understanding what that looks like in the organization you’re about to join. 

Damien: It’s so funny you’re saying Northern British Columbia because that was part of a territory that I had, I don’t know, 20 years ago.

And you have to find, you have to find, it wasn’t a foresee company, it was a shipping company. TK shipping and they were doing very well just in the oil trade. And so it was you have to, even if you have to polish some things that might not be as as nice as maybe someone in who has the Manhattan territory you just have to make it work.

And I think that’s again, where the. Where the grit comes in, not everything is going to be handed to you. Speaking of very large organizations I just read a report where Ernst and Young was forecasting a 20 percent increase in MNA activity in 2024. And actually just in Q1 of this year they saw a 36 percent increase in, in those MNA deal values.

I know that you’ve been through a bunch of these with Eloqua and Oracle and, different M& A activities. One, so two part question. One, what do you make of the current state of M& A activity? And second, what advice do you have for professionals that might be going through one right now or anticipating 

Jason: one?

Yeah, two very different questions. 2023, the debt markets, the interest on debt was growing exceptionally. So that meant the deal values had to come down in order Facilitate or finance a deal, right? Private equity firms, which represent a significant portion of M& A transactions, use debt financing as a particular vehicle to purchase companies.

I think what’s happened is the interest rates have softened. I talked to private equity firms every day, multiple times a week. And, the general thesis is, Hey, the markets are frothing, right? They’re starting, we’re starting to see this improvement in the M and A transactions, a lot of it driven by the interest rate on debt.

And most of your viewers probably don’t care about debt interest rates. The net of it is yes, 2024 will be a very hot year for M& A acquisitions. I think we’ve all read the alphabet or Google looking to purchase HubSpot. There was an Informatica. Slash Salesforce conversation. SAP just bought walk me for a couple billion dollars.

We’re seeing more and more private equity transactions happening. And I think we’re going to see a lot of MNA transactions occur throughout the course of this year and beyond. I think we went through the lull and we’re coming back up and we’re going to see a hot market. Especially when I talk to the PE guys and they’re always saying, look, we think the markets are frothing and that’s usually a strong indication of.

A lot of acquisitions about to take place going through an acquisition. I’ve gone through lots. I’ve bought companies, sold companies, we we exited CDC software to Vista private equity firm, rebranded it to Aptian. I left that job and went straight into Eloqua thinking, Oh, no more M& A for a little bit, because in my tenure at CDC, we had bought something like 13 companies in the course of two years, which was insanity.

And then I joined Eloqua and the first day on the job, my CEO says, we’re going public. We go public and the first quarter out, we have Oracle sniffing at us who ended up buying us. And that was a real cultural shift. And my, I would sit and have coffee with the sales organization and say, You have to understand the culture is going to change moving from a hundred million dollar company to being part of one of the world’s biggest software companies, but as a seller who carries a quota.

Opportunistically, can I make hay? Can I make some money in this new environment? As long as you learn to adopt these new tools, new process, new ways to get deals approved, new management, new expectations. But we went into Oracle as a hundred million dollar business and I left, three years into it and we were 750 million organization and a lot of people made a lot of money along the way.

And I think if you’re opportunistic and you understand the situation your company’s in and why the acquirer is buying your business and then your CEO should be articulating high level what the thesis is. We’re, this particular private equity is buying us to put fuel to the fire. They’re going to add money to marketing and to sales and to product.

Okay, now we’ve got some more wind at our backs pushing us forward. Or in the case of the Eloqua to Oracle, the acquisition was to start the Oracle marketing cloud. And it the culture was the biggest shift for the Eloqua business. We, Eloqua, everyone had stickers.

Culture eats strategy for breakfast on their laptops and you get into this big monolithic machine and something as simple as a deal approval. And I know you, you worked at Oracle, right? You’ve got to write, a novel to make sure that you can get the discounts and the concessions on the deal.

And it doesn’t take 20 minutes unless it’s a hundred million dollar transaction. The average rep is waiting one, two, two and a half, three weeks to get their deals approved. In a lot of cases, they get rejected. And understanding that there’s nuances and differences. And a lot of people ask me why I stayed.

And I said, I’m opportunistic. I looked at this as an opportunity to go and take what was at the time, the market leader. According to Gartner and Forrester and AMR and all the analysts, and we were seeing amazing success. And walk it into accounts and sell million dollar plus transactions because of the power of the company that purchased us.

And that’s a really interesting place to be as a seller. You put all your emotional things on one bucket and say, I don’t want to be there because it doesn’t have the culture, the office is changing, my tools are changing, blah, blah, blah. But in the other bucket, I have a quota. I have to get to my quota.

I’ve got a good territory and now I’m part of an organization that can propel me into driving, not just to my quota, but well beyond my quota. And if you take the money aspect and the success factor, I would say to anybody in that situation, look at it from that perspective, learn and be a part of a really big company and decide after.

A year, if that’s the place you want to be. 

Damien: And I think the culture cultural change aspect is a huge part of it. And I think we’re seeing another wave of change coming through with AI and just maybe one or two big things that you’re thinking AI will change for salespeople. What do you think would, will be happening in the next six, nine, 12 months?

That is going to be either really good or really bad for salespeople in terms of AI. 

Jason: So I think for B2B SaaS sellers, I don’t think AI is going to displace their jobs and, be able to transact in understanding business problems and solving those problems with the solution. AI is a vital component to the future.

And I think about, You get a new lead, a new opportunity that’s coming. We talked about the scions and you get them at the early stage and you think about the research that an individual has to put into understanding that business, what they’ve gone through, who they’ve bought, who they’ve sold, what’s happening at the executive level.

And AI can synthesize a lot of the research element of the job. You can use that AI to identify prospects quicker at the top, tippy top of the funnel, change your messaging to be more in line with their business. And then at an executive leadership level, my hope and prayer is that you can have AI tell you the predictability of your pipeline based on characteristics, demographic information about your prospects because the one thing that’s tried, tested and true in this business, Damien, is when you play outside your ICP and your ICP is built over years of selling your software to different types of company, early days, you’re opportunistic, hitting everybody up and down, and then you get to the steady state of going And I know what my ICP is and when we did analysis, but it took humans and ton of work, our win rates were dismal outside of our ICP.

And so being able to look at something as simple as, is this company in your ICP? Are they, are they showing signals that they’re interested in buying this technology? All this other information that we have to try and glue together to assess. A pipeline, but when you’re in a small company, probably easier, smaller pipeline as a sales leader, you can go through and triage the entire pipe, the type of companies.

But if I go back to my Oracle days, our pipeline was pages and pages of deals. And you’re relying on individuals and humans to extract what the value of the pipe is instead of using technology that says, Hey, this is the rate wouldn’t it be nice to know this is the range we predict this to be based on characteristics we understand of how you sell.

And I think AI is going to play a vital component. Into doing that. 

Damien: I think that I think it already is. We’re using tools internally that are doing that for us to be able to give us not only the data, the firmographic or the demographic data around these, but also the activity. Hey, what is happening? Not only the activity from the customer side, but also from the seller side.

Hey, are they saying the right things? Are they introducing pricing? Too early or too late. Are they talking about the value in the right way? And all of this is now being crunched on the AI side and saying, Hey, listen, you got to be aware of this, or you’re talking too much, which I often do, but it is all these things together, I think is going to be super helpful in terms of B2B sellers and B2B and B2C sellers as well.

I know that we’ve been talking for a little bit. I have one last personal question for you. You’re, you are a traveler, Jason, you are always on the road. You’re going flying all over the place. You’re getting up at 4 a. m. As you said, and, maybe. Flying to, to wherever, what’s your favorite place to visit both professionally and personally?

Jason: And you’re not going to love my answer. Most people, it’s Chicago. I love Chicago. Back in the day when we worked together we had, a fairly significant presence for our company size in Chicago at One East Whacker. It used to be called the Unitran building, I think it’s now the Kemper building, and I was flying in and out, sometimes I would drive from Toronto, and I started bringing my family, to Chicago, because I was spending so much time there, and, you start to see a different side of the city that, sometimes you’re in the back of an Uber.

And you’re on your phone doing messaging, you look up and you say, Oh there’s a certain landmark or something. And then you get to experience a city for what it is. And for me, it’s Chicago, hands down. Lou Malnati’s, 

Damien: hands down. The Malnati’s pizza, that’s the best. Very good. And then personally, what’s your favorite place to go personally?

I think, take a guess at the answer, Damien. I would say something that was built by Walt Disney, I think. Or, because you got the four kids, or something tropical. Someplace tropical. 

Jason: Yeah, I love the heat. I do, but I have a soft spot in my heart for Orlando, Disney is a big part of it.

I think you know the answer, but I’ve, we used to go two, three times a year with our kids. Enjoy pool time, go to Disney and the parks. I became very fascinated with the Disney company. And when. Oracle purchased Eloqua. We had just bought Disney University passes, and I had a chance to go learn from Walt Disney World, which further grew my fascination with that particular business, but I love Orlando tropical.

I love Hawaii, I went to Croatia last summer split and floated in the Adriatic for nine days, and it was unbelievable. So I think 

Damien: any place hot, yeah speaking of hot, it’s, it’ll be a nice hot summer. So Jason, thanks so much for your time. Have a great summer. Good luck with all of the the kids getting into either work or trouble, hopefully a little bit more work than trouble, but we’ll speak to you soon.

So Jason, thank you very much.