EPISODE 610: Deep Sales Success Advice from Women in Sales Leadership Award Winner Alyssa Merwin Henderson from LinkedIn

The Sales Game Changers Podcast was recognized by YesWare as the top sales podcast for 2022. Read the announcement here.

Subscribe to the Podcast now on Apple Podcasts!

Become a partner of the elite Institute for Excellence in Sales (IES) and take your sales team to the next level!

Purchase Fred Diamond’s new best-sellers Love, Hope, Lyme: What Family Members, Partners, and Friends Who Love a Chronic Lyme Survivor Need to Know and Insights for Sales Game Changers now!

Today’s show featured an interview with the Institute for Excellence in Sales 2023 Women in Sales Leadership Award Recipient Alyssa Merwin Henderson., Global Sales Solutions at LinkedIn. The interview was conducted by IES Women in Sales Program Director Gina Stracuzzi.

Find Alyssa on LinkedIn.

ALYSSA’S TIP:  “Optimize for learning and development in your career. Take every moment you can for professional growth, to learn something new, to shadow someone who’s doing something exceptionally well. The more opportunities that you can take to really invest in learning, especially early, but of course throughout your career, the more opportunities you will give yourself over time.”


Gina Stracuzzi: It is my pleasure to welcome Alyssa Merwin Henderson. She is VP of Global Sales Solutions [at LinkedIn]. Welcome, Alyssa.

Alyssa Merwin Henderson: Thanks, Gina. It’s so good to be back.

Gina Stracuzzi: We always like to let our guests tell the listening audience a little bit about themselves and how they got to this spot. There are great highlights in your career, obviously, that won you this award, this acknowledgement of all the great things you’ve done. Give us some highlights.

Alyssa Merwin Henderson: Thanks for the opportunity to share, Gina. I hope it’s a journey that is both inspiring and relatable because I started my career as a BDR, so entry-level salesperson learning to cold call. Back in the day, that was the approach and I was smiling and dialing and really learning how to engage with senior executives at an early stage of my career. Had an opportunity to progress from a BDR into an account executive sales manager. About 10 years into my career, had the opportunity to join LinkedIn. I’ve now been at LinkedIn for about 12 and a half years, and continued to just take on opportunities as they came up.

I will say, my story is filled with ups and downs and zigs and zags and plenty of learnings along the way. Oftentimes we look at people’s LinkedIn profiles, or we look at their careers from afar, and we think it’s just been an up-and-to-the-right journey. I think the reality is much more dynamic and filled with lessons and sideway moves, lateral. I think all of that has really led to where I am today, which is leading LinkedIn sales solutions business, which is a job I could have never really dreamed of even having. I’ll leave a little bit of that for us to dig into if we want, but it’s just to say there’s so much more to the story for all of us, and I think a lot of the learning and growth comes from those moments of challenge.

One thing I’ll share that’s a bit unique is I’ve actually only worked at two companies so far. I spent about nine years at my prior company, and it’s been about 12 and a half years so far. I think that longevity has actually also been really important, because it’s given me so many opportunities to build relationships across the company and take on new challenges.

Gina Stracuzzi: Both things you said there are really great acknowledgements, because I think it was Sheryl Sandberg that said, “Don’t think of your career as a ladder. Think of it as a jungle gym.” It’s something we talk about in the forum a lot, those lateral moves you can learn so much, but the longevity is something that doesn’t happen a lot anymore. Then people get frustrated with their careers, but if you’re jumping a lot, it doesn’t give people a chance to really know you.

Alyssa Merwin Henderson: That’s right. I think that as you get further in your career, you also realize that the body of work takes time. Whether you’re a strategic account executive who’s managing large complex accounts, it takes time to build those customer relationships to demonstrate value, to build credibility. You can’t do that in one or two years. You often are going to need to spend many years in a role to demonstrate excellence, deliver value, and to have a proven track record. That becomes even more true as a manager. I think that that’s one thing that many people maybe are a bit shortsighted about as they find themselves ready for the next thing. But I think we often need to step back and say, “Is my work here done? Have I delivered on the promise of what I can do and all I can achieve in this role and have I delivered for myself, for my customers, for the company I’m working for?”  

Gina Stracuzzi: I need to have you come and speak to one of the forum sessions which I do. I have sales leaders, women who have made it to the top of their game, come in and talk about that. It’s not a straight line. Some of it’s dirty and scrappy and not always fun.

Alyssa Merwin Henderson: Definitely scrappy.

Gina Stracuzzi: What do you think are the qualities that best highlight your trademark approach to sales? How do you think that’s helped you coach others that you manage, especially women?

Alyssa Merwin Henderson: Well, Gina, I mentioned I have had lots of learnings and made mistakes and had hard moments in my career. One of those was learning really early on that showing up and being vulnerable and being real and being my true self for my team was one of the things that was going to most help me to connect with them. I learned that by not showing up that way early on in my career. I think that over the last probably 10 years, one of the hallmarks of how I lead is from a place of real vulnerability and authenticity. I think that in this day and age, we’re all looking for connection. We’re looking for meaning. We’re looking for purpose. We want to work for and with people that we respect and can relate to and feel that they care about us. That’s the kind of leader that I want to be, and that’s the kind of environment I want to create. Of course we need to deliver and we need to work hard, but I don’t think those are at odds. Those are a couple of the attributes that I hold really, really dear to me. We’ve been able to create an incredible organization of leaders who lead from that similar place.

Gina Stracuzzi: Certainly, it’s funny, day and age gets used no matter which generation it is, but I think post-pandemic, everybody’s feeling wounded in ways that they can’t even fully appreciate. Having a leader that’s willing to be a bit vulnerable probably gives people openings, which is great. Let’s switch gears a little bit and let’s talk a little bit about what’s going on in your sales organization today and what are some of the biggest issues and how are you solving those?

Alyssa Merwin Henderson: Well, so much has changed over the last few years. I heard one customer refer to the pandemic as the sugar rush, which I think is such an appropriate way to think about it. It was a time when customers were throwing budget at challenges. Everyone had to move to a virtual selling environment overnight. Companies were just trying to figure out how to survive. We’ve moved through that period and we’re now in what we call The Great Rationalization, where customers are pulling back and they’re being much more thoughtful about where they’re spending their scarce resources, about how they’re investing. They’re also trying to simplify often some of the tools, technology, and investments that they’re making.

You have that dynamic, and then you also have changing buyer behavior when it comes to how much of the buying process they’re doing on their own. In fact, salespeople are really only influencing that last 5% of the sales process, because so much of the due diligence and the research is happening on the buyer side before we ever walk in the door. These dynamics are really creating an incredibly high hurdle for value delivery from the sales rep. What I mean by that is it’s no longer enough to just engage with a customer or a prospective customer with knowledge about your solution and what you can offer, and just trying to close the deal and move on. We’re really having to engage with a different level of preparation, of understanding. It’s harder than ever to break through the noise of all of the outbound messages and engagement that these folks are getting. It’s really causing reps to have to say, “How do I show up in a way where I can add value, even if I’m not able to win the deal?”

One of the things that I talk to my team about is, how can you win mind share even when you’re not able to win wallet share? Because I think if you’re one of those individuals that can bring a perspective, an insight to a prospective customer, even if you don’t win that deal in the moment, you are likely going to be someone that is going to be able to engage with them or perhaps win that deal down the line when the timing makes sense. I think these are all of the types of things that we have to adapt to this moment that we’re in, and to how the buying behavior is changing and how in this macro environment, it’s also causing us all to have to rethink how we’re showing up.

Gina Stracuzzi: We even see it on a micro level in the institute. You’re right, people are so much more thoughtful about what it is they’re doing. I think it’s hard for the buyers too. They’re trying to figure it all out and make it all work. We have this ever-looming potential of financial disaster. We’ve been talking about it now for a year, and that unknown makes it difficult for everyone to figure out like, what’s the best next step?

Alyssa Merwin Henderson: It is. It’s so difficult. I think that in sales, it’s such a wonderful and hard role. I think one of the things that we have seen over the last 12 months, and something that we introduced to the market last year, was this concept of deep sales. Deep sales, it’s the antithesis to the cold call, the shallow approach, the spray and prey that so many of us that grew up in the industry, and probably a lot of companies still employ to some degree. But this idea that with the proliferation and so much more technology to support outreach, the volume of outreach is suffocating for many of us who are on the receiving end, and so we just stop replying. We stop engaging. Deep sales is saying, “Let’s pause. Let’s take a step back and instead of high velocity transactional engagement, let’s spend a bit more time doing due diligence so that when we do reach out, we have something compelling, insightful, and engaging to say, and the chances of a good outcome are much, much higher.”

Deep sales focuses on three elements. One is relationship intelligence. The second is account intelligence. The third is buyer intent. How can we help you get engaged with the people who can make formal introductions? I call them hidden allies. Let’s think about Gina, for you, someone that you used to work with that is maybe at a company you’re trying to sell to. You’re going to have a much higher likelihood of getting engaged with that company. If you reach out to that former colleague, they can give you the lay of the land. They can give you the insider tips. They can make introductions. That’s a great example of a hidden ally. How about a past customer of yours that’s now a decision maker at another company you’re trying to sell to? That’s an amazing hidden ally because your last best customer is your next best customer. Those are the kind of insights that we certainly can provide through Sales Navigator, but just broadly, we would want all sellers to be embracing that approach of let’s be smart about how we’re engaging and who we are engaging. But it’s not just enough to know who someone is. You have to have the context for what’s going to be compelling for them.

Gina Stracuzzi: Well, you’ve managed to answer quite succinctly my next question, which was how have things changed? I want to know a bit about how Sales Navigator can help companies overcome that. But I also want to know some of the biggest challenges you’ve seen for women in the last three years, and how are they coping with that? How has this changed maybe to deep sales and more thoughtful selling? Are there benefits for being a woman in that? Do you feel like the nurturing more patient approach that women have will suit them well in this?

Alyssa Merwin Henderson: Well, I think that women have some innate skills, and I’m making a big generalization, but they generally tend to have some great innate skills that can make them exceptional salespeople and leaders. I do think that the skills needed to be successful today are probably the same skills that have been needed all along. It’s really doing your upfront due diligence and research, really caring about understanding your customer’s challenges, being incredibly curious, being an incredible active listener. Then also having a perspective beyond just what your product does. Today, in this environment, in this world, people want to know not just what you offer, but they want to know if you have a perspective on the space, on the competitive set. I think having a balanced somewhat objective perspective, if you can manage that, is really helpful. Because at the end of the day, you’re really a coach to your customers. They should be making the best decision that’s right for them, whether or not it ends up being a sale for you.

I think that all of those skills or qualities are things that both men and women can do equally well. But I think that those are so important today, again, when there’s so much access to information. They need someone who can coach them through the decision making process. What are the questions I should be asking? What are the pitfalls I might experience if I go with this solution versus another? To the extent that you can be helpful in helping them think through and ask those questions, I think you’re going to be in a great place on the other side of it.

Gina Stracuzzi: Well, in as much as this is the Women in Sales Podcast, I want to continue down that road a little bit and talk about what advice you might have for women in sales professionals right now, especially those that might be just starting their careers.

Alyssa Merwin Henderson: Well, my advice, again, absolutely for women, but for anyone, is really to, number one, look for the kind of company and culture where you’re going to feel supported, where you have people that you can look up to that you feel like they’re creating an environment where you can thrive. Often for women, again, women and everyone, but women in particular, there’s a real desire for flexibility, for autonomy. They want to be invested in, they want to be seen, they want to be able to be mentored, they want financial security. I don’t think any of this has changed, but I do think it’s at the forefront of driving flexible work arrangements and it’s really creating a lot of opportunity for women that’s really wonderful these days.

The other advice that I would give is become a subject matter expert in whatever industry you choose to sell in. I mentioned this a minute ago, but study your competitors, understand the full ecosystem and consume all of the relevant industry content so that you can really show up as an expert, not just in your product, but in the space. Then make sure that you connect to all of your prospects, your clients or customers on LinkedIn so that you can continue to engage and invest in those relationships, both in person or virtually, and of course, on places like LinkedIn.

Gina Stracuzzi: Your sales team overall, not just women, but just your sales team, what are your expectations for them and from them? Are you expecting them to do all these things? Are they doing them, are they doing those deep dives and learning? Working for LinkedIn, you certainly have all the tools at your disposal, Navigator being one of them, obviously the biggest. How do you instruct your team to use those resources?

Alyssa Merwin Henderson: Well, we do have a mantra of live what we sell. Because we sell Sales Navigator to other sales organizations, we absolutely want to be best-in-class at using it ourselves. We want to do a great job of understanding the ecosystem and the space, not just Sales Navigator, but who are the others that are in the similar categories, and adjacent categories? Because oftentimes we and others are competing for wallet share, even if there’s not a direct competitor that offers the same type of product. But that’s not always clear to your customer, and it doesn’t mean that you’re not still competing for those limited budgets, especially in this environment like we talked about. Those are some of the things that we talk about, are how do we make sure that we become the best examples of living what we sell?

I’ll tell you a quick story. These stories are so powerful when you can bring it to a customer. I was recently in Europe spending some time with some of our reps and some of our customers. One of our very top strategic account managers, she was telling me about this amazing deal that she had just closed, but it was a deal that took years. She had tried to get engaged with a very senior decision maker and had really struggled to get engaged with him. She was following him in Sales Navigator, turned out that they were in the same city on a business trip. He had posted on LinkedIn, “I’m in Milan this week for a customer conference.” She said, “I’m in Milan as well.”

She reached out to him, they ended up grabbing coffee. That coffee turned into a couple of conversations later, and it ended up being one of her biggest deals of her career. The only reason that she was able to engage with that individual is because she happened to get that account insight about where he was and what he was up to because he had shared that on the platform and she was following him on Navigator. I think that’s just such a great example of living what we sell. When she brings that story to her customers, they can understand, gosh, I can imagine how powerful that would be if all of my reps had that same insight about their customers. That’s really where the power of being able to tell those stories and having the personal experience with whatever it is that you’re selling or whatever the example is for your industry.

Gina Stracuzzi: You’re right, nothing sells like a good story. It absolutely is true. I love that and congratulations to her. Let’s talk a bit about customers. What are they looking for from you now that things have changed now, when you can cut through the noise as you were discussing earlier?

Alyssa Merwin Henderson: Well, again, it goes back to if a customer or prospect is completing 95% of their due diligence before you walk in the door, they already know all of the players in the space, at least the ones they want to be considering. They have probably great connections and people in their network where they can go to for references, to ask questions. What they’re looking for from a salesperson is really, again, that hold my hand in the last mile of my decision. Help me understand. I’m down to probably two or three vendors, help me make a good decision. That’s really what they’re looking for from a salesperson today. Again, what are the pitfalls I should be looking out for? Help me and really be open and really direct and honest about what are some of the challenges. Let’s talk about implementation. Let’s talk about what success would look like and how hard it is to achieve success with the different products.

I think they’re really looking for all of us to be experts on the entire space. Again, not just on the one product or set of products that you sell. No one wants to be messing up and making bad investment decisions in this environment. The best thing we can do is help them to feel like we’re minimizing the likelihood of a bad investment. How do we minimize risk? Maybe that’s the best way to sum it up.

Gina Stracuzzi: It is all looked at as risk at this point, whereas before they might have had X number of dollars for sales tools, and if it didn’t work out, well, we’ll just try something else. But that’s certainly not the case anymore. We are at that point in our conversation where we like to ask our guest, Alyssa Merwin, your last piece of advice as to what sales reps or managers can do in their career today. Just one thoughtful step they can take to take their careers to the next level.

Alyssa Merwin Henderson: Gina, I’m going to give you two. One is optimize for learning and development in your career. I mean take every moment you can for professional growth, to learn something new, to shadow someone who’s doing something exceptionally well. The more opportunities that you can take to really invest in learning, especially early, but of course throughout your career, the more opportunities you will give yourself over time.

The second piece of advice that I would give folks is to remember that our careers are presumably quite long. Think about the arc of your career. Oftentimes we find ourselves optimizing for short-term decisions, but if we zoom out and we really think about what’s the timeline or the horizon that I’m thinking about, whether it’s taking a new role or changing companies, really thinking about, is this going to help me build a set of skills or experiences that over the long arc of my career are going to help me build towards something really exceptional and really gratifying? Versus necessarily taking a job because it’s a better title or it’s paying more money.

Those are the types of decisions we often can take that actually set us back. In the short term, they may feel like they’re moving us forward, but actually can sometimes set us back more than we want. I’d really encourage people to think about always making decisions to that lens of assuming it’s a long arc of your career, what are the skills, experiences, even if the title or even the pay isn’t as compelling, that will help you make leaps and bounds over the longer arc.

Gina Stracuzzi: That is great advice, Alyssa. Thank you so much for joining us. I can’t wait to see you at the awards event and to be part of bestowing the award on you. Look forward to that. We will see you all again next time on the Women in Sales version of the Sales Game Changers Podcast. Thank you all for joining us.

Alyssa Merwin Henderson: Thanks, Gina. Thanks everybody.

Transcribed by Mariana Badillo

Leave a Reply

Your email address will not be published. Required fields are marked *