If sales people hope to stay competitive in the industry, they need to stay on top of the latest and greatest tech tools in the game. In the latest episode of the Mindtickle podcast, Ready, Set, Sell, Hannah and Tony sit down with Jacki Leahy, the Head of Revenue Operations at Winning by Design. Specializing in solving startup growth challenges and streamlining business practices to uncover insights and drive growth, Jacki has plenty of sales wisdom to impart with listeners. During this episode, Jacki shares more about her career background (hint: it’s an unexpected one), offers her tips for adopting new tech tools that can help you hit your targets, and lets us in on all her best-kept sales secrets. She also provides some advice for sales executives hoping to find their niche and play to their strengths to optimize performance.
Tony: You know how the world of tech continues to evolve at a rapid pace. And salespeople need to keep up with the changes if they hope to stay competitive in the industry.
Hannah: But it’s not always easy to stay on top of the latest and greatest tech tools in the game. That’s why people like our guest today are so valuable in today’s ever-evolving landscape.
Who is Jacki Leahy?
Tony: Jacki Leahy is the head of tech experience at Winning by Design. She specializes in solving startup growth challenges in streamlining business practices to uncover insights and drive growth.
Hannah: In other words, she’s tapped into all the most cutting-edge tools, platforms, and technologies that make it easier to do what we do best: sell.
Tony: And she’s here today to share more about her career background. And I’ll give you a hint, it’s an interesting one, and offer her tips for adopting new sales tools that can help you hit your target.
Hannah: Thanks for joining us today. Welcome to the show, Jacki.
Jacki: Thank you, Hannah. Hi, Tony. Hello.
Hannah: What I’d love to do is start off by understanding a bit more about your career so far. And, more specifically, that moment in time when you realized that you’d become a scrappy chaos wrangler.
Jacki: I switched over to tech at the tender age of 33 so I’d lived a full life before coming over to the tech world. I started out as a kindergarten teacher, and you cannot run a classroom without embracing that there will be chaos. And it’s your job to herd the cats and get them going in the direction that you need. No doubt, you will not be set up for success… but you need to make the day successful.
Hannah: I love that you said you lived a full life before the age of 33. What made you make the transition to tech?
Jacki: I was doing real estate. I did it for a few years in Manhattan. So exciting. And then I moved back to Boston, and I had the best quarter of my whole career selling condos. And I realized I could do whatever I wanted to do. I had figured it out. And realized I don’t want to do that anymore,
Tony: It seems like you’ve had a lot of different roles across a lot of different industries. And I think my favorite actually might be, per your Twitter account, an over-caffeinated Salesforce magician. I have a two-part question for you. First, how are you able to stay so versatile and flexible? And would you consider yourself someone who’s willing to try new things?
Jacki: I think people are either specialists or generalists. I know I’m a dabbler. I like to know just enough of a language to make friends and order a drink. And then on to the next. Other people really want to take a deep dive and know CPQ [configure, price, quote] or something very specific. I would much rather know about the parts and how they best compose. And then, more importantly, know who to ask. Yes, I love to try new things.
Hannah: Tell me how you landed your role at Winning by Design. What drew you to that company specifically?
Jacki: I’ve been a huge fan of Jacco van der Kooij for years. I saw him speak at the Outreach Conference in 2018. What’s so compelling is that it’s a mathematical model for how to do a recurring revenue business. As for me, give me the what or give me the why and I will figure out the how.
It is beyond exciting to be at a place where everyone else is figuring out the what. Then I just get to bring in the how, like how do we make that come alive for the end user? And how do we make that appealing for the frontline manager? What will they need to see, touch, feel, and do, and will we be able to make this scientific approach a reality?
Hannah: How do you stay motivated? And how do you stay positive? It’s been rough the last few years, let’s be honest. Tell me a bit more about that.
Jacki: For me, it’s a very conscious decision to choose joy, to choose connection, and prioritize that. It is so seductive to go into a complain-y loop but that has a cost. Don’t get me wrong, I can complain with the best of them. But what are we doing? What are we focusing on? Would you consciously wake up and decide, “Today, I’m going to sprinkle poopoo everywhere I go.”
Tony: It’s a lot easier to be negative, but it’s so much better if you can find that positive connection. That’s really what’s going to advance the ball. So I totally agree with what you’re saying there. I think there’s a lot of validity to that to that point. Can you say there has been any running theme or common lessons that you’ve seen across the different spaces you’ve been in that can really apply to someone’s career path?
Jacki: Really getting clear on who you are and what your talents are is important. For me, a big thing was taking the DISC assessment, and even bigger was the CliftonStrengths. I think it costs $100. Most of you listening to this have professional development budgets but even if not just take it. It’s a pretty long multiple-choice test and at the end, it spits out this essay on who you are, how you operate, what’s important to you, and who you are in the world. When mine came out the first line was “When do we start?” And I thought, “Yes, oh my gosh, my number one talent is as an activator so let’s put me in situations where an activator is necessary.”
Tony: You bring up a point that I’ve advocated over the years: investing in yourself. If you can’t invest 100 bucks in yourself, then what are you really doing with your career and with your path? That is such a simple, small thing that you can do but look at what it’s it’s done for you. It’s got you to where you are right now. You can really understand where you can go and the easiest way to get there with the most joy. There’s so much that can be done.
Hannah: I’m trying to piece together a little pattern here. I’m thinking chaos wrangler to activator and then we come to solving problems for startups and growth companies. How do you bring all of that into those spaces? This is a podcast where the majority of the audience is going to be people in sales or people who are thinking about sales. And these startups need to sell. How do you come in and bring all of that jazz and that joy and get them moving?
Jacki: Well sometimes it’s not welcome. I’m specifically thinking about when I first entered tech sales.
I think a sales career is like a cheat code. You don’t have to be a superstar. You don’t have to do the big whales, but hit your number, consistently. Don’t be a jerk. And even if you don’t see yourself as an AE — that’s an account executive — that’s okay. Find a spot in sales where you can just crush it.
For me, I love outbound business development. I will cold call, I will interrupt people’s days all day and find it fun. So find your spot in the Model T Ford factory of sales that’s what you can do, even if it’s making sure that they’re using the product and they renew next year. And you can think of it as a side hustle if you don’t see yourself as a rep for your whole career. You don’t have to know what it is you do want to do — just put yourself in situations where you are. Just keep your eyes open, keep your ears open. Talk to people across the company — talk to engineering, talk to product, etc. — and you’ll pick up on patterns.
Hannah: Tell me more about what you love about your job. You go into a startup company… and it’s obviously at a point where they’ve said they need help.
Jacki: They admit they need help from the outside and they trust you. And nine out of 10 times they’re going to tell you what’s actually happening because you’re the outsider and you’re the confidante. It starts out as a Salesforce problem but it’s never Salesforce.
Tony: As you’ve been working with these different companies, what would you say is your overall strategy for helping them streamline their business processes so they can really focus on customer impact and important things like that.
Jacki: Listen to what’s going on. If you’re so inclined, do a data analysis. Think about what will make the biggest impact and where the biggest friction point is.
Hannah: What kind of top tips, tools, platforms could you recommend or what do you usually talk about when it comes to removing unnecessary friction?
Jacki: Well, if you are the person in I.T., or business operations, or even revenue operations, make sure that you have end user buy-in and not just a check-the-box buy-in. They’ll know whether or not you really attempted to solve their issue. I think that goes a long way. It’s like if your server never really checked if there was blue cheese dressing — I’m okay with ranch, but did you ask?
Tony: Jacki, just coming on the podcast today shows how much you want to connect with others in the community, really saying, “I’m a part of this and we’re all in this together.” What would you say are some of the top benefits of engaging with others and what things have you learned or helped to teach other people?
Jacki: Oh, my gosh, my career is only a reality because of the friends I’ve made along the way. A few years back, I didn’t know what revenue operations were, but you make friends and they introduce you to other friends and you don’t have to pay a million dollars to do a Salesforce course, you just learn it. And you join some Slack communities, join the Salesforce Trailblazer community, and when you’ve got questions, people want to help. I do feel this sense of a karmic responsibility to then pay it forward because I would not be where I am if not for the people who really invested in me being here by doing things like jumping on a Zoom call to explain what Process Builder is when I didn’t know. Yes, I wouldn’t be where I am if not for the amazing people — and the more you put into a community, it’s wild how much you can get back. I joined Pavilion about a year ago, based on a friend’s recommendation. Put yourself in situations where there’s a spirit of excellence. Just get yourself around those people and ask them what’s up.
Tony: I spend a lot of time on LinkedIn and there’s a great community there. When I first joined LinkedIn, many years ago, I just thought it was some way to put my resume out there but now the more that I get engaged with it, the more addictive it becomes. When I hear the ding signifying that someone’s reached out to me, I immediately jump on it to see what questions someone has or find out how I can add to a conversation. I’ve even helped people find jobs — and it becomes, like you said, a karmic thing, a pay-it-forward sort of scenario. There are great things we can do together, if we all give a little bit of our time.
Jacki: Exactly. But don’t do it at your job’s detriment. If you want to be helping people or mentoring people, set aside a reasonable amount of time — because you’re a lot less helpful unemployed.
Hannah: Keeping up with the ever-evolving technology that makes up the landscape, specifically in the sales space, is expensive, and there’s a lot of duplication. What tech gets you excited? And how do you make sure you’re always on the cutting edge? Where do you go to make sure you’re in front of it?
Jacki: Well, to the average person, please don’t feel the pressure to have to stay on top of it all. I do this because I love it. You don’t need to be in the know. If you really need to evaluate tools, there are people who can help you. I have a problem with the phrase ”tech agnostic.” I will recommend the right tech for you without a kickback or anything but I am passionate about tech.
Staying ready for change
Tony: Things are changing all the time. How do you stay focused and make sure you’re staying on the things that are going to build the most value for an organization?
Jacki: If you’re an operator at a business, please look at your revenue engine map. It’s so tempting to think, if you love outbound, for example, what if we had a chat bot? But you might not have a problem with lead generation or conversions. Meanwhile, you don’t have anyone to hand things off to or that sort of thing.
Really look at all of the spots in your journey, look at the conversion rates, where are things falling down? And look for benchmarking, like free Google. If you’ve got the budget, hire a consultant to look at your turn ratios and benchmark that.
If you’re an operator of a business, please be responsible and don’t just do what you’re already good at. Look for the weakest links.
Hannah: That seems so simple, but it’s not. I’d love to hear about some of the common misconceptions or the crazy myths that you encounter in sales.
Jacki: Like Salesforce doesn’t know what you need? It’s not conspiring against you. I remember being a BDR and wondering, “Why aren’t my IRA meetings showing up on the chart?” Well, it’s basically just filtering and showing you records that meet the criteria. Try not to take it personally and get to the bottom of what it is picking up and spitting out. It’s just a query.
Tony: What advice would you give to other sales professionals who are really trying to hone in on their strengths and find a similar path to what you’ve done? What would you say to somebody who’s struggling and looking to find their career.
Jacki: No matter what age they might be, I’d say “get yourself to a Tony Robbins event, unleash the power of the UPW [Unleash the Power Within] weekend, just be in the presence of possibility. I also loved the Landmark Forum. I just got so much out of that. And I’m doing a new thing called the Atlas Project that’s coming up this weekend. I’m very excited. If you’re in sales, like join, um, Corporate Bro. It’s like sales savages. It’s like Reddit, but for salespeople. If you’re very curious and you’re hearing this, LinkedIn message me, I think I have some invites. It’s awesome, right? If you’re in ops, join Wizards of Ops — it’s a community. If you’re in tech, join Civilian — there’re courses going on all the time. There’s a channel for every topic, right? Get in there, ask your questions, meet people. And networking events are coming back. I went to a Chili Piper– hosted dinner last night and got to meet all these salespeople from Boston.
Hannah: What are you excited about when it comes to sales? Tech, just everything in our space? Or what can you already see unfolding?
Jacki: I love that end users no longer have to do anything to get data captured. Data capture just happens, where you happen to be and with so much more contextual guidance. I don’t want to have to open up a wiki to figure out how to best ask this question. When I’m on a call, I want contextual guidance.
Hannah: I’m loving that in the B2B space, we’re finally stealing everything from B2C. It’s taken a couple of decades, but we’re getting there. It’s almost becoming the norm.
Jacki: We’re getting there. It’s possible. Anything’s possible.
Tony: You said you’ve got Atlas coming up, but what else is next for you? And for Winning by Design?
Jacki: I was brought into Winning by Design to do what I was just talking about. They have all these incredible playbooks and methodology and strategy. What I’m going to be doing is baking it into a whole process. With the tools inside your Salesforce, you’ve got the right things to measure and the things to measure them with. So, yes, I’ll be baking that all in.
Tony: We’ve learned a lot here today… but we’re not done yet. We have our rapid-fire questions to go. Hannah’s going to start and we’ll go through these really fast.
Hannah: Okay, Jackie, tell me your sales philosophy in three words.
Jacki: Interrupt their day.
Hannah:What’s the best piece of advice you’ve been given in your entire career?
Jacki: Sometimes there’s nothing for you to do.
Tony: What is your top productivity hack?
Jacki: Zero inbox.
Tony: What is your top prediction for the sales industry in 2022?
Jacki: Automatic capture.
Hannah: What’s one thing you believe is revolutionizing the sales world today?
Hannah: You spend a lot of time inside the sales organization. Please share one piece of advice.
Jacki: Figure out what works and blur out the rest.
Tony: What would you say are the top two tech platforms (aside from Salesforce) that you couldn’t live without?
Jacki: Google Calendar. Slack.
Hannah: Are leaders made or born?
Jacki: I think it takes both. You might be born with the personality and characteristics or the trauma that makes you take fearsome responsibility and ownership. But I think if you really do take that seriously, then you develop that as well. You can’t just rest on the laurels of your leadership.
Tony: Jackie, thank you so much for your time here today. This was a pleasure. It was fantastic hearing your stories and about your evolution as a professional here.
Jacki: Thank you so much. This was a great way to start my day.
What have we learned?
Tony: I don’t know about you, but I absolutely feel more positive and optimistic just from this brief talk we had with Jacki.
Hannah: I was definitely bouncing in my seat. And I think I smiled and giggled throughout the whole episode, to be honest. Jacki has some really great tips and insights for any listeners out there who are hoping to simplify their day-to-day roles and streamline business practices overall.
Tony: Exactly. I’m Italian, so I can verify that Rome wasn’t built in a day. So why should a business be any different? Jacki’s advice of taking a slow and methodical approach to streamlining business practices made a lot of sense. And I think it really helps to drive home the importance of making data-driven decisions.
Hannah: I’m all about data always. And I know you are too, Tony, but you have to identify the pain points in your business first, so you can set your team up for success and simplify the customer experience overall.
Tony: Exactly. You need to find the friction points. That’s where you’ll find the biggest opportunities to create an impact in your business, and zero in on ways to maximize your outcomes.
Hannah: Jacki also reminded us to always keep the end user in mind, which is great advice for anyone, no matter which area of the business you’re operating in.