#019 Mastering Modern Sales Strategies with Adam Jay

Thomas Miltschuh: Welcome to our new episode of Speak Revenue. Remember, revenue is not a goal. It's a result, but a result of what? In this show, we turn our eyes from the output towards the inputs. We speak to sales leaders and entrepreneurs about their journeys. Join us on our quest to uncover and learn the root causes of success. Let's unpack what works for them and what didn't today with our guest: Adam Jay. Hi Adam, welcome to the show. Great to have you here. Thanks for the time.

Adam Jay: Hey, Thomas. Thanks for having me, man.

Thomas Miltschuh: Awesome. I think we can get, just get started right away. Let us know who you are, what do you do? Why are you so successful?

Adam Jay: Oh, I don't know about that last part. But who am I? I am , I call myself a recovering CRO. I am a seven time VP of Sales, multiple times CRO, who has spent a lot of time in the startup space and realized that founders are given bad advice all day long. They don't know how to properly transition from founder-led sales. And the common answer that I got at almost every startup I worked at was just go hire more people that'll fix the problem. So I decided to do something about it. About six months ago, I left the startup world full time. Launched Revenue Reimagined with my business partner, and we are a full service go-to-market fractional agency, covering everything from marketing, sales, success, RevOps, and everything in between.

Thomas Miltschuh: Awesome. Maybe, you could elaborate a little bit on your previous positions. If you want to.

Adam Jay: Of course. I was the CRO for a series of startups out of Seattle called Falcon, which was a revenue intelligence automation platform. Think, competing with Clari ,Outreach, Gong, SalesLoft of the like, came in super early trying to establish product market fit. prior to that I'd spent time in everything from hospitality tech. I worked for Toast, and was part of a very successful IPO there. And then did a couple of sales tech startups in the demo space. I worked for a company called Reprise, and I have the startup bug man. The saying is true. The average sales leader is at a startup, no matter how good or how bad you do is 12 to 14 months. Every 12 to 14 months starting something new and building it is hard. But when you love to build, that's what you do. So transitioning that passion for building, but not wanting to start over every time I was like, fractional leadership's the way to go. I get to work with great founders, a ton of different businesses every day and help them avoid the pitfalls that I've seen. Unfortunately, it ruins so many startups.

Thomas Miltschuh: Okay. Sounds impressive. So it looks like there's a lot of experience you can share with our audience. I'm really looking forward to diving deeper there. Maybe first of all, could you give us a big picture? What are the goals for this year? What are your goals for next year?

Adam Jay: Ooh. So our North Star goal is to help as many founders as we can increase their runways. Decrease their dilution. That's a big goal, right? There's no tangible number. And any sales leader will tell you that's not a goal, right? A goal is an actual number. So for us, you know, by the end of this year, we aim to have helped 25 founders.

Thomas Miltschuh: Mm-hmm.

Adam Jay: Um So that's 25 engagements starting from April through the end of the year. That puts us slightly over capacity. But we have a great network of folks that we work with. Next year the goal is to really scale out the agency. So we want to do, you know, anywhere between 20 to 50, startups and founders per 6 month period. Some of this Thomas' project work. We do have folks who will reach out to us and ask just to help with an ICP, but the majority of it is true fractional engagements, building out their entire go-to-market function, and like I said, helping to increase that runway and decrease that dilution.

Thomas Miltschuh: Okay. so usually we talk about, sales process. Could you step us through your sales process or maybe some common example you see from lead generation over closing to upsell and maybe some pitfalls? talk 

Adam Jay: Now, the sales process is, it's a vague term, right? Like we try to call it specific, but everyone's like, oh, we have the sales process and my process is MEDDPICC, or my process is Challenger. That's not a process, that's a methodology. Is the first thing. I was talking to a founder yesterday and he said, we'll only hire you if we could use MEDDPICC as our sales process. It's not a process, it's a methodology and P.S: it's a methodology from the nineties! But that's a whole separate conversation.

Thomas Miltschuh: That's right. 

Adam Jay: What I see as the biggest pitfall when we're working with founders who really do understand that you need a repeatable and scalable process is number 1: lack of documentation. They don't get all of this knowledge out of their head from when they were selling, to bringing on sales reps and really documenting what takes place at each stage of the process and why. And then the second biggest thing I see, Thomas, is a lack of clearly defined entrance and exit criteria. And it sounds like I'm being difficult or I'm being a process freak or whatever. But if you think about this, one of the things that's really important is being able to understand, and articulate your pipeline. And where deals are. And if you don't have entry and exit criteria, what I think is a deal that's in, we'll call it negotiation. It might very well be in discovery because we haven't met the criteria for it to be in that stage. You have to work with your reps to understand that. And then lastly, the way that I try to align that with sellers that I'm working with, if you are my customer and I ask you where you are in your buyer's journey, that answer better damn sure map to where I have you in Salesforce or HubSpot. Otherwise, we have a huge misalignment, 

Thomas Miltschuh: Do you also focus on the whole buyer journey, like, the customer success as well? Customer attention.

Adam Jay: We do, so as a full cycle go- to- market agency, we do everything from lead generation all the way through NRR. So starting with demand, working through to getting the qualified leads in the door, getting them converted to sales, what does that handoff look like to onboarding? And then ultimately, how do we expand them and renew them?

Thomas Miltschuh: Maybe we could talk a little bit about, go-to -market approaches. These days I often see people mentioning traditional go-to- market approaches or methods that don't work anymore, like cold calling compared to a few years ago, or cold emails. Is there any trend you see any reason for that you could mention? Do you agree with it? 

Adam Jay: So cold calling is not dead. And cold email is not dead, but the way that it's been done and the way that it's being done by most companies is still dead. It's funny, I actually got a cold email right before we started recording. It was so good that I responded back to the seller complimenting him, like, this is an email that actually resonates! And I'll get back to that in a second. But what you typically get is this email that says: " Hey Adam, I see you're the CEO at Revenue Reimagined, and you must be trying to build out and blah, blah, blah, blah, blah, blah, blah, blah, blah." It's the same as saying, "Hey Thomas, I see you breathe oxygen. Let's talk." It doesn't work. Buyers are inundated with cold outreach right now, and if you don't find a way to stand out and be hyper relevant and speak their language, you're going to fail. But more importantly than speaking their language, it's gotta tie back to needs. It's gotta tie back to big rocks, big business values and priorities, because even 6, 12, 18 months post the Covid Pandemic. We are still in a market where people don't wanna spend money. We're still in a market where people want to shrink their tech stack, where the CFO has to approve every single deal. So if you're going to get to that CFO and P.S: You have to multi-thread! Because if you don't get to the CFO, you have no chance of a deal sending an email that says: Hi, I see you're the CEO of, or you're the VP of Sales of, or you're the director of engineering of... isn't going to resonate! I think when it comes to what outbound looks like today, there's a few things you could do to stand out from the noise. Use the phone. I cannot emphasize it enough. I take cold calls every single day. I'm not gonna tell you I take every cold call, but if you call at the right time and I'm not busy, I'm gonna answer the phone probably 'cause I'm not a hypocrite. Be relevant and be respectful. Know your shit. Spend five minutes researching someone before you call them or before you email them. And make that email short and sweet. Too many sellers, founders, BDRs, and even in success Thomas, like this. This translates not just to cold outreach, but even into expansion. They look at the email as the goal of this email is to get you on the phone with me to book a meeting. Bullshit! The goal of a cold email is to generate interest. Period. The end. And when you shift your mindset to the goal being to generate interest, your email goes from being this long, to being this long, and you now are gonna start to have a conversation. All you want is a response, not a meeting.

Thomas Miltschuh: Right. Looks like you also need to have a specific plan on what to talk about with people. What resonates with them, and not only a plan, but also a strategy to even be able to follow a plan.

Adam Jay: You, you have to. I mean, listen: at the end of the day, volume used to work, right? Outreach, SalesLoft, Groove. And I'm not trash talking about these platforms. I love all of them. But what they did is they created this environment of just dropping everyone in a damn sequence and everything's gonna be fine. It doesn't work. Like you can't put everyone in the same sequence. You have to personalize. You have to know. What you're talking about. More importantly, you have to know and understand the struggles that your prospect is facing so that you could speak to their struggles. Listen to their CEO's podcast recordings. If they're public companies, read their 10 Ks. If they're startups, go look at their reviews, go look at G2. Go listen to what their customers are saying. So you could tie back very specific examples because as I told someone who reached out to me, When I was at Falcon, the assumption was, oh, you're the CRO at a series A company, you must struggle with this. That wasn't my struggle at all. Every CRO at every series A company does not struggle with the same shit.

Thomas Miltschuh: That's right. Yeah. You can just throw a tool into the team and start using it and then hope everything gets better. Seems like you really need to align it with your own goals, but maybe even more important with the goals of your target group, of the people you want to talk to. 

Adam Jay: It's funny, the sign behind me, and I don't know if you could see it, because on my screen, I can't, but it says: "tell me more." It used to say: "Hope is not a strategy". Customers did not like that but hope is not a strategy at the end of the day. You can't just throw everything at the wall and see what sticks. You have to have a specific strategy for all aspects of your go-to-market funnel, starting with demand and going all the way through expansion.

Thomas Miltschuh: Right. Talking about tech stack, what tools are you using or what would you recommend throughout the buyer journey?

Adam Jay: So it's a great question and it's highly dependent upon your business. Upon your stage and upon your funding. So for us, we are bootstrapped, right? We're an agency. We are never going to, you know, go out and raise venture capital. so consider us like a seed stage company. We use HubSpot for our CRM. We use Monday for all of our project management and collaboration, with our partners and our clients. We use Lavender every email that gets sent out goes through Lavender. Nothing that's below a 95 is allowed to be sent .Extremely important. AuthoredUp, manages all of our LinkedIn, and then we utilize Canva for all of our graphics. and Stripe for payments. When we're working with most of our customers, we specialize in Seed to Series B. So the stack's a little bit different. It could be HubSpot or Salesforce. I have a love and hate relationship with both of them for very different reasons. Typically for sales engagement. What I'm seeing is clients either using Groove, are really making an inplay into the market, especially with the Clari acquisition. Outreach is still increasingly popular. and then Mailshake is a pure sequencer. I had a lot of clients who were considering Apollo as well. They're obviously up and coming. They just raged a hundred million dollars, but you definitely need some type of sales engagement platform, not to just go mass email people. And then one of the things where I think people overlook, and you don't wanna buy it too early, is a success platform. Something like a Catalyst or a ChurnZero. Catalyst only works with Salesforce. ChurnZero could work with Salesforce or HubSpot. But you need a success platform so that you could track that customer journey as well. And Calendly can't live without Calendly. No one should live without Calendly. 

Thomas Miltschuh: Right. That seems to be pretty comprehensive suggestions. So if you just use those tools and get started, you have everything you need.

Adam Jay: Yeah, you have everything you need. The tools grow as you grow, right? For example, you know, maybe at Seed and A you're using HubSpot, but as you grow into B and you become more complex and have more complex billing motions, and you need more complex contracting pricing and quoting. You need to migrate over to Salesforce. We're working with a client now that is a $50 million printing company. So non-tech think like the labels that go around these tic-tacs, they print them, they couldn't do their business on HubSpot, Salesforce is the entire ERP. So it varies from business to business. I look at tech stack recommendations, Thomas, just like I do a sales process, we're never gonna come in and say, great, you're series B: use this! You still need to do discovery and understand what the needs of the business are.

Thomas Miltschuh: Yeah, yeah, sure. Very individual as well. Maybe as you get so much experience. This is very interesting. What have you tried that comes to mind first? That did not work. 

Adam Jay: Related to what? Related to sales? Marketing? Success? I mean, that's a big question. I failed a lot in my life.

Thomas Miltschuh: You can pick something. It could be sales, could be marketing, could be business in general.

Adam Jay: So let's go marketing. One of the things that we tried at a previous company, we were very focused on building community. I think community is important and it's a strategy that most companies need to implore right now. And a lot of them are doing it wrong, just like I did it wrong. We had thought that the way to go out and build community was to stand up a slack group. To go hire, you know, 5, 10, 15 evangelists on LinkedIn, get them to start posting, you know, for us obviously at a compensated rate. And that the leads would come and it didn't work, and there's no doubt why it didn't work. Just because someone has 30, 50, 70,000 followers doesn't mean those followers are in your ICP. Doesn't mean those followers have any need for your product. It doesn't mean that person is a respected voice. To help drive decisions. 30,000 followers doesn't mean you're a respected voice. It could just mean you're funny. Maybe you are a respected voice. So I found that utilizing that strategy of, Hey, these people all have, you know, we'll just say 50,000 followers and we'll pay them 500 bucks a post and the deals will follow. Was a colossal waste of money. When I tell you we didn't get one single viable lead because of it. That is exactly what happened, and the flip side and the lesson learned from that evangelism are important. I think that it absolutely has a play and you need the right people. But the way to do evangelism is to seek out thought leaders within your industry who have actually used and benefited from your product that could speak to the real results. Them and their teams have seen. That's very different from paying someone and I have no problem paying people. I think that people should be paid, but it's very different for me to reach out to you. Have you posted about your experiences with my product and help me try to get business by actually being a living, breathing, posting testimonial versus the post that everyone knows, which is, Hey, such and such product is so great, and I love it. And they know that you never ever, ever, ever used it. it. goes back to storytelling. It was a very, very, very expensive lesson.

Thomas Miltschuh: Yeah, I think that's really interesting. There's a lot of noise on LinkedIn, for example.

Adam Jay: It's an echo chamber. 

Thomas Miltschuh: It seems to be still, somehow a valid business model because it is still used and pretty common.

Adam Jay: Listen, we get the majority of our business on LinkedIn. I think that if you do LinkedIn right, it is incredibly valuable. LinkedIn right, is posting valuable content that resonates with people and can help people. It's engaging with other people's content and having conversation. LinkedIn is the biggest community out there. That said, there's also a lot of noise, right? and what you don't want to do is be the person that, you know, just throws noise up there. But I think as much as it's an echo chamber, if you know and choose. Who to follow, who to seek advice from, who to engage with. it could be extremely beneficial to your career no matter what that career is. I've gotten great clients off of LinkedIn. I've made great friends off of LinkedIn and I've seen people close multimillion dollar deals that started with a post they made seven months ago that someone happened to see that resulted in someone following their content. That when there was a need resulted in, Hey Thomas, like I, you wouldn't know this, but I saw this post you made six months ago and started following, you know, your journey and what you're speaking about and you know now there's a need for whatever product you're selling. Would love to have a conversation with you. It happens every single day.

Thomas Miltschuh: Yeah. Yeah. Great. You mentioned this, in most cases, it's rather easy to separate professional from unprofessional postings or activities.

Adam Jay: You mean LinkedIn is not Facebook?

Thomas Miltschuh: Yeah. Just maybe a little bit. 

Adam Jay: It happens every day. 

Thomas Miltschuh: When did you realize the community creation project didn't work and how?

Adam Jay: Yeah, we were probably about three months in, we'd spent enough money. The number doesn't matter. The evangelists were asking for more money, like they loved us, right? Like we're reaching out to them and saying, post more, post more, or post more. and when we started looking at our funnel, or lack of funnel and lack of pipeline, it was a hard reality to understand that like we'd spent tens of thousands of dollars and had not one viable lead to attribute to it. and I actually know the exact moment that I realized it wasn't working. We had someone that had posted about our product, had commented in the threads that like, oh, this looks great. I would love to have a demo. I actually had reached out to that person 'cause I saw it first instead of someone on my sales team. And they responded back to me and I'm very surprised they said what they said, but they responded back and said, oh, thank you so much for reaching out. I was just trying to help my buddy, blah, blah, blah, out with engagement. Really have no need for your product. That did it for me. Because if this person was telling me that how many people are engaging, that would never be honest enough to say that it was the giant red flag that was like, this isn't working. All that I'm doing by paying this person to post is pumping up their engagement, their follower account. It's not doing anything for my business. 

Thomas Miltschuh: This sounds rather painful. You've already mentioned the lesson learned, as it is so insightful. Maybe you could even mention something that didn't work, regarding sales.

Adam Jay: There are so many things that don't work regarding sales. It's a volume game. I absolutely back in the day was the sales leader that would just say, call more. I think that's probably a cop out answer. I think we all know that. To me, You know, if I'm gonna look at what doesn't work in sales. Recently for my team, we had tried to get back to in-person events too quickly post covid. We had heard on LinkedIn, go figure. that people want to be in person. They want to have real conversations. So we figured why not, you know, have an event and bring people together to learn about our product. And we didn't plan it out properly. We didn't understand. In the remote environment that we're in, events are hard, right? they used to be easier. You could do these events, people would get on airplanes and there's still some that are wildly successful. You know, SaaStr was great, Dreamforce was great, but as an individual company for one particular product, people aren't gonna come on a plane to come to your dinner. Like it's just not gonna happen. and we had a marketing leader that was pretty insistent that it would work. I'm not one to , I'll push back certainly, but at the end of the day, I'm not gonna step on toes. And if that's how they wanna spend their budget, like I'm okay with that. And we went all in on this round table that we were trying to host about whatever the, I won't give the topic away 'cause it'll give the company away. but about the topic we were trying to host and we sent invitations out to like 250 people and three people responded that they would be interested in. Like that's a pretty low conversion rate. Based on feedback from LinkedIn that people want events, what should have been done. And what I was encouraged to have done was rather than again, going back to the echo chamber and saying, you know, there's 30 people on LinkedIn who say events are great. Reach out to our customers, reach out to our prospects, ask them what they want, where they want to be met, how they want to have conversations. Do they want to have an in-person event? What the broader LinkedIn community wants is highly irrelevant to what our specific subset of customers wants. It was an epic fail on the sales side because it generated no pipeline whatsoever.

Thomas Miltschuh: Yeah, and I think both examples, the community example and also the event example. Of course it's important to, to learn the lesson, whether it's some cost in the end, it's a waste of money, but also can really demotivate the team. Right?

Adam Jay: That's the most important part. listen, money comes and goes. Right? And I get that we all want to close deals, raise more money, ultimately have some type of exit event, but at the end of the day, money comes and goes. What doesn't come and go as freely is team morale. And when you have a sales team, Or a marketing team or a success team, and you don't elicit feedback and you try things that ultimately don't work. They start to lose confidence in the leadership. Then someone quits, then another person quits, and eventually you become this piranha of a company where it's like, well, why do I wanna work there? No one lasts more than X amount of months. Too many leaders don't take the morale impact into play, when they're building sales orgs.

Thomas Miltschuh: So, so many insights. So, so many experiences you've learned from, do you have a kind of a framework you would suggest, when you start with a new client, for example, to, optimize to, to start consulting?

Adam Jay: Yeah, so we have a proprietary framework that we use for all of our clients. We call it Align, and it's kind of our guiding principle of how we do business. We are very big into data, and not, coming in and saying, because we did it here, we're gonna do it there. And, it's a one size fit all approach. So we start with the scale audit. We really want to understand where your business is. There's over 150 different questions that we ask. A lot of them are yes and no or rate, on one to five, but it gives us a good picture of the business. We then take the time to deeply learn. So we're gonna interview employees, we're gonna interview customers, we're gonna do all of our research on the company. the rationale is that the why is just as important as the what, right? Like we need to understand you very, very detailedly. Based on our learnings, based on the audit, now we're actually gonna start to implement some changes. We're gonna start to drive some scalable and repeatable processes and start to optimize those using a feedback loop. Feedback's really important. I think a lot of advisors, a lot of consultants will go in and just do what they do because it's worked before and they don't seek that feedback. So we utilize a feedback loop that ultimately leads to growth. And where I think we are different from most is at the end, even after we roll off of our engagement, we will continue to partner with you to nurture, to refine, to tweak, and to continue to grow that relationship so that you could start to see your business generate some of our time together. 

Thomas Miltschuh: That's great. I feel like too often sustainability's under, estimated. Yeah.

Adam Jay: Yeah, absolutely.

Thomas Miltschuh: Great. is there any additional lesson learned you would like to share with our audience? No matter if it's, addressing CEOs or sales reps starting their career?

Adam Jay: Yeah. I think no matter what your role is, whether you are a CEO, a BDR, an AE, it does not matter. There's a few things that are really important. Listen, more than you speak. You are given two ears in one mouth for a reason That doesn't change. The more powerful you get in the company, listen to your teams. Listen to your people. Take feedback. And the other one that I tell everyone is, you, you cannot ever have a coach too early. I waited until way too late, in my career to have an executive coach. Everyone should have a coach. Yes, it's an expense. A lot of companies will pay for it, but you need someone on the outside who doesn't have an interest in the quote unquote company, but has an interest in you. To make you better, to bounce ideas off of and to have very candid conversations, and help you grow as a professional.

Thomas Miltschuh: Right. Yeah. Thank you very much. Thanks for all those insights. I'm really thankful we are able to provide so much value and actionable insights to our audience. I think it was an awesome episode. It will be great for our listeners. We can come to the end actually. Alright, everyone that brings us to the end of this episode of Speak Revenue. I want to thank our guest at Adam Jay for joining us today and sharing such valuable insight. A huge shout out to all our listeners, your support means the world to us. Remember to check out our website: speakerrevenue.com for a full transcript and additional resources, and if you enjoyed the show, please leave us a review on Apple Podcasts or wherever you go for your listening needs. It really helps get the word out. Also, follow us on LinkedIn and Instagram or on YouTube. We'll be back soon with another great guest. Until then, stay curious and keep listening.