EPISODE 591: Digital Media Sales Opportunities with HW Media’s Jennifer Laws

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[EDITOR’S NOTE: This Special Women in Sales episode podcast , hosted by Gina Stracuzzi, featured an interview with Jennifer Laws of HW Media.]

Find Jennifer on LinkedIn.

JENNIFER’S TIP:  “Make sure that you have the right people in the right place. Be willing to say, this person does not fit our rubric, this person does not fit in our world. We are going to cause ourselves more pain than the revenue is worth and we need to walk away but we need to focus in on these people who are the right customers. Doing that and working in concert with your clients has been a recipe for success for us.”


Gina Stracuzzi: Today my guest is Jennifer Laws. She’s Senior VP of sales at HW Media. As Fred alluded to, this is the first time we’ve had someone in media sales on the podcast. I’m super excited about this. Over the last couple of months, we’ve had a couple of new industries which we really enjoy hearing about. Jennifer, welcome.

Jennifer Laws: Thanks, Gina. Great to be here.

Gina Stracuzzi: Wonderful. As you were laying out for us, media sales is unlike any other kinds of sales. Most of our listeners are B2B enterprise salespeople. Tell us what makes this different from standard sales of that nature?

Jennifer Laws: Yeah, absolutely. I think there are a lot of things that are the same. Sales is sales and everybody knows that really, if they have a job, they’re in sales in some form or fashion. But what makes media sales different especially from software sales or platform sales, SaaS sales, those types of things, is media does not have recurring revenue.

Maybe it’s important to take a step back and define what I call media. Through my career, I have worked for different companies, advertising agencies as well as various publishers, and out of home media companies. So out of home being outdoor billboards as well as advertising in airports. When I talk about media, it’s the advertising that is running alongside content that a publisher might be putting out.

HW Media is a publisher for the housing industry. My team sells the advertising that is adjacent to the content along with event sponsorships. Our clients, their priorities, their tactics, what they want to accomplish year to year change, and unlike a SaaS based enterprise level sale, we don’t have a contract that just simply renews. We have to redo the contract and essentially resell that customer every year.

Of course, we have long standing relationships and relationships are really, really important. We do have a concept of a renewal, but it is completely start from scratch, let’s build this campaign again and the revenue that we get from it could vary vastly. We work really hard to have net growth in our client base, but it varies vastly. The lack of recurring revenue is really the difference.

Our sales cycle is very sporadic. We have some that come in very quickly and do a spot by and it’s one thing and it’s kind of over and done with. We also have clients that buy for a whole year. Buy the quarter, buy first half, second half. There’s a lot of variables that some other sales professionals don’t have to juggle that media does have to juggle.

Gina Stracuzzi: I can remember actually, and I hadn’t thought about this in years but really early, early, early in my career, I sold radio advertising and I hated it. It just seemed kind of at the time, now, mind you, this was way more years ago than I care to even think about. It was not expensive, really. Radio advertising is actually a pretty cost-effective method. It just seemed like the companies that we were serving, they were local companies, they just were trying to nickel and dime everything. It’s not that I don’t appreciate it but it’s a lot.

Jennifer Laws: Radio is a particular challenge. That’s not a particular sector that I have ever sold but I have had people on my team that have come from a radio background and boy, if you can be successful in radio, you can be a successful salesperson. You learn a lot of skills, and you are scrappy, and you are hungry and motivated and are willing to turn over the stones and pound the pavement to find new business. That’s a really important skill that you have to have in radio.

Gina Stracuzzi: Yeah, for sure. Right out of college I didn’t hear that. I was not that hungry. Let’s step back just a little bit and tell us how you got to the point where you’re now so immersed in media sales. What brought you here?

Jennifer Laws: I would say I kind of follow the opportunities. When I first graduated from college, I knew that I wanted to do advertising and marketing. That was always something that I wanted to do. I early on was in promotional marketing, worked for an ad agency that did logo merchandise. Very kind of entry level roles, bottom of the barrel, kind of the gopher type of role and just fell into the next opportunities as they came along and recognized that sales was where you had control over what you were doing.

There was a lot of glitz and glamour, of course, when you’re in your early to mid-20s. You think that taking clients out to dinner or traveling is all glamorous and that’s what I wanted to do. I’m like, “I want to go do that.” You have to be in sales to do that. I took the opportunities as they presented themselves, but then really fell in love with digital media specifically, and had the opportunity about 17 years ago to join the Wall Street Journal.

That was an amazing opportunity and really learned a lot from being there and really honed my craft. I sold outdoor airport advertising before that, and that was maybe really scrappy and made me understand what client service was all about and how you went. This was long before we had the internet. I remember printing out MapQuest from appointment to appointment.

I had to build my own media kits and your suitcase was four times as heavy when you went out on your trip than when you came back because you didn’t have digital media guys or anything. Laptop was weighed a million pounds. Going to the Wall Street Journal allowed me to have exposure to a global media company, and exposure to print as well as digital and ended up really falling in love with digital but also had exposure to tremendous leadership and tremendous opportunity to work with companies across the country. I was much more opportunistic than I was planned and calculated and never thought I would be in sales but it’s kind of evolved along the way and now it’s something that I’m really passionate about.

Gina Stracuzzi: Yes. Interestingly enough, I did advertising sales many years later, magazine advertising sales specifically for publications like the Screen International. Screen International is like a Hollywood Reporter but in Europe and it was great. I really enjoyed it. I got to go to all these great film festivals and it was really exciting.

Print advertising sales is a really interesting animal because you meet all kinds of people and the businesses are very different. You get to meet a broad swath of people. If you’re at B2B enterprise, you’re meeting different people but they’re all doing the same job. The Wall Street Journal must have been an interesting way to learn the business.

Jennifer Laws: It was. I started out there and I sold advertising to high end luxury car dealerships, as well as yacht brokers and private aviation companies. It was definitely an interesting category to start out in. I also covered what they called legal notices, so that’s bankruptcies and class action notices, and those types of things that have to do with all the companies that are publicly traded. Then I ended my time there in the recruitment and employer branding category. I kind of hit all spectrums.

Gina Stracuzzi: My career has been very much like that. I followed opportunities more than I had this plan. I have to say and it sounds like you’ve experienced a lot of the same things, Jennifer, that it’s exciting in that you’re learning so many aspects of something. Then you end up where you’re supposed to be as you make your way along this, somebody’s dropping some more little crumbs for you to follow. I’ve loved it because it’s taken me all over the place.

Jennifer Laws: It’s been great and it was a great training ground there. Like you said, I definitely feel that the position that I hold now and the company that I’m with now, the publisher that I’m with now, it’s really exciting and I’ve worked hard to get where I am, and to have the seat at the table and everyday grateful for that. But know that I’ve worked really hard to get here every day. That’s the thing about sales especially in media is you have to work hard every day and that’s one thing in control. What is your activity and how much effort are you putting into it? This isn’t a profession for coasters.

Gina Stracuzzi: That’s a good saying, I like that. Thinking about what we just talked about, can you highlight like the three best decisions you’ve ever made in your career?

Jennifer Laws: Yeah, absolutely. I think that one of them is always being willing to explore the opportunity. As a salesperson, I think that means that you always have to be listening for when there might be an opportunity to work with a client, listening and trying to understand what they might be doing, and how you might be able to work together. A salesperson has to be a consistent networker.

On a career side, I think that means that you are always willing to have a conversation. That doesn’t mean and I’m not telling everybody to all of a sudden, anytime a recruiter reaches out to you that you should have that conversation. But you have to understand how you are going to progress through your career and be strategic about it and have those opportunities. I would not be in the position that I’m in now, if I hadn’t been willing to have a conversation.

I had been laid off from the Wall Street Journal. I was looking for a new position but I knew nothing about the publication that I’m with now. It’s a B2B publication and hadn’t heard about it before and didn’t know much about the housing industry, except for I own the house. That was it. I took a leap of faith because the conversations that I had with the CEO and owner were fantastic. I got really excited about his vision and about what he was driving towards. Taking that leap of faith and taking that opportunity to have a conversation even though I was having concurrent conversations as you do when you’re looking for a job with companies that are household names. Having the confidence to have that opportunistic conversation throughout my career in different reasons has been really, really important.

Second, I think is listen and ask lots of questions. I am always the one who raises my hand and says, “Can you explain that further? Or I’m not quite understanding or what about this? Have we thought about this?”. Ask questions, listen to the answers and be thoughtful about what you are doing, but also, listen, learn and watch and observe. Who do you emulate? Who do you respect? Who are you going to choose to be a mentor? Who are you going to choose to model yourself, your behavior, your career after and what qualities do they have that you admire?

Then I think the last and I wrote this down as I was preparing for this is always be ready for what’s to come next. Always be prepared and open for what’s to come next. If your company approaches you with a new opportunity, or an evolution of your role or something needs to change in the organization, things change really, really quickly in the media world and I would imagine the overall sales they do as well. Be open to that. What’s the worst that’s going to happen? Be open to change. Don’t be resistant to change.

Gina Stracuzzi: Those are great pieces of advice, truly. You gave us one example where you decided to speak to someone that was less well known and it turned out to be a great decision. Can you give us some examples of perhaps a time when you didn’t listen to your own advice and you regretted it?

Jennifer Laws: I don’t have as clear of an example of that but I think in sales, there’s an opportunity to second guess yourself a lot. Should we have approached that client differently. Should we have approached that sale differently? Should we have said yes to that discount? Should we have made this concession? Whatever the question is, we always can go back and play Monday morning quarterback.

But one of the things that was shared recently with me is, you can’t fault yourself from making the decision that you made at the time with the information that you had at the time. You can’t hold yourself accountable for a decision you made in the past with information that you now have. You didn’t have that information before. You made the best judgment call and the best decision at the time.

Now, if it was the wrong decision, you have to learn from that, but don’t beat yourself up by second guessing your decision with new information that you didn’t have at the time. I think in sales you have got to remember that things move very fast and you are trying to drive revenue, hit a goal, drive new business, serve your customers, nurture your customers, develop relationships.

There’s a lot of things going on, and you are doing the best that you can every single day. Don’t be so hard on yourself. That is something that I try to remember every day. That is a piece of advice that wasn’t in my three top decisions but that is something, that you made the best decision and if it wasn’t the right one, how are you going to correct course and learn from it but also give yourself a break.

Gina Stracuzzi: Let’s talk a little bit about 2023 and what that’s going to be like, and what’s your mantra moving forward, Jennifer?

Jennifer Laws: That’s something that we’ve been talking about for a couple months now. How are we going to prepare? Everybody knows that this is a difficult economic time. But our mindset here at HW Media this time of the year and moving into 2023 is how can we steal market share? How can we help our customers steal market share, because we know that we are positioned to come out of this more strong than we were when we went into it, and we want to help our clients be the same way.

The thing that we’re really focused on and I’m focused on is controlling what you can control. What’s in front of me today that I can control? What can I do to make a positive impact on today, and tomorrow will take care of itself. But what can I do and control? So that’s activity, that’s effort, that is just going the extra mile and doing all those things. I can’t control some things but there are certain things that I can control.

There’s the old saying that says, you can’t fight the Fed. I can’t change what the Fed decision is going to be but I can control what I do each and every day to output that. I think there’s a lot of things that sales organizations can do. There’s a number of things that we look back to and revert to in terms of our high-performance sales organization mantra of making sure that we’re prepared, making sure that our value prop is there, making sure that we understand why our clients are buying from us now and why they’re returning to us. That may have changed as may have our ideal customer profile.

What are we thinking about? Who are the customers that are in activity now and how can we best serve them? These are the things that we can control? These are the things that we’re focused on, and they’re going to get us through, and we’ll be best positioned to help our clients make it through as well.

Gina Stracuzzi: That is great advice. I really liked that you can only control today. Don’t worry about what’s out there next, make today matter.

Jennifer Laws: Right. That’s easier said than done. I’m awake at 3am too. I don’t have all the answers. I’m awake in the middle of the night too but I’m trying to minimize the fallout on that one.

Gina Stracuzzi: Yes, absolutely. In just a minute, I’m going to ask you for one piece of advice that people can put into place today from your point of view to help their careers move forward faster. But let’s just take a minute to talk about sales leadership and what you think are some of the most important things that a leader can do for their team.

Jennifer Laws: I think that’s a really good question and I think that’s a question that sales leaders try to figure out each and every day. I think it starts with your hiring process. I think it is having the right people in the right positions, and then letting them do what they do best.

One of the things that I battle a lot is I want to jump in under the idea that I’m helping. I’m not always helping, I’m micromanaging and meddling. I’m holding on too tight under the guise in my own head that I’m helping, not helping. I know I’ve hired great people. I know I hired really seasoned salespeople. Let them do what they do. Let your managers and your vice presidents who are on your team and your deputy, so to speak, let them do what they do great.

That is something that I have to remind myself all the time, but I think sales leaders can empower their people and that’s how it’s going to make them great and make everybody else better. But I also think sales leaders are about supporting the team that they have built. In an HR sense, yes, they work for you but in reality, I work for them.

How can I make you successful? I’ve set a task for you. You have to hit this goal. This is how we all get compensated. This is what we’re here to do. How can I help you get there? That is a mind shift, is a I’m here to help you. My day is your day, my day is not my own. My day is your day. How can I help you? But you have to be careful that that help is actually helpful and not meddling and that sometimes I go a little bit far and people have to say, “Okay, Jennifer, we got this.”

Gina Stracuzzi: Well, it’s good that you recognize that and you don’t double down when someone says, oh, because I’ve had managers like that, we’ve all had managers like that.

Jennifer Laws: I’m all for the feedback loop and I’m happy for constructive criticism. It’s not easy to hear but it makes us do better.

Gina Stracuzzi: That’s wonderful advice. That can be something that we could use as our last piece of advice for sales managers is to keep a hands off but make sure your people feel supported.

Jennifer Laws: It’s a difficult balance to strike. Most sales managers and sales leaders were salespeople at one time, and salespeople like to control. As you move up, and you have a team that you are leading, it’s hard to relinquish that control. You know you can get it done the way you think it should be done but you have to let them do it and let them be successful and I want them all, nothing but success for all of them. I know I’ve hired really great people and let them do their thing. I work on that every day.

Gina Stracuzzi: That’s a brilliant thing. That makes you an outstanding leader. Oh, yeah, it is hard for sure. But the best people know it’s hard and do it anyway.

Jennifer Laws: Yes, absolutely.

Gina Stracuzzi: Is there anything else you’d like to leave the audience with before we part our ways?

Jennifer Laws: I would say as you are thinking about your sales organization, your sales team, however you define it in your world for 2023, one of the things that has been most helpful for me is making sure that you have the right people in the right place. You have a scalable and repeatable process, and you know who your customers are and be willing to say, this person does not fit our rubric, this person does not fit in our world. We are going to cause ourselves more pain than the revenue is worth and we need to walk away but we need to focus in on these people who are the right customers. Doing that and working in concert with your clients has been a recipe for success for us.


Transcribed by Mariana Badillo

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