The First 100 Days of Switching from Sales to Marketing with Nicole Penland, Reciprocity

Career paths are rarely straight lines. But, when is it the right time to leave your decade-long career in sales… to join marketing?

Nicole Penland recently joined Reciprocity Inc. as the Director of Demand Generation a few years after making the jump from sales to marketing. She joins us to discuss how her sales experience helped her create revenue-generating programs and how one book set her on the right path for her first 100 days at Reciprocity.

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The hosts:
Trinity Nguyen
Christian Kletzl

In this episode, you’ll learn:

  • How sales experience helps marketers
  • How to prioritize your goals during the first 100 days
  • Why you need buy-in from your teammates and how to get it

What to listen for:

  • [02:00] Switching from sales to marketing
  • [06:22] How inside sales experience helped Nicole’s marketing career
  • [07:07] Nicole’s first 100 days blueprint
  • [09:04] How to prioritize goals
  • [11:14] A mistake to learn from
  • [14:13] Migrating sales and marketing functions
  • [15:53] The importance of buy-in from your teammates
  • [17:53] How to know when you’re ready for the next step

Check out this blog post by Nicole: "Why Sales is the Best Start to a Marketing Career"

Reference Links:
Guest headshot

Nicole is an award-winning marketing director with a demonstrated history of working in the computer software industry. She's innovate, fearless, bold, leader with the ability to implement a customer first approach, diversity of thought, and unity of action.

Read Transcript

Nicole: I knew I needed to take a very, very great team to even greater success. So I spent some time working on the blueprint for what that would look like and identifying the key areas that I thought could make the biggest impact and got buy-in. And I have to say that's one of the keys, as you're making any sort of changes, is socialize it and get buy-in before you go ahead and make that change. So, I did just that.

Trinity: Welcome to the First 100 Days, a show for revenue practitioners by revenue practitioners, giving you unscripted access and exclusive resources to help you navigate any new transition or initiative. I'm Trinity Nguyen from User Gems. And not long ago, another member of our team, Nelson Gilliat, had a chance to speak with Nicole Penland.

Nicole is the Director of Demand Generation at Reciprocity, a risk and compliance platform. At the time of this interview, Nicole had recently joined Reciprocity, just a few years after making the jump from sales to marketing. How did she make the switch? You have to hear from Nicole. Take a listen to her conversation with Nelson.

Nicole: I would say I cut my teeth in sales is where I started. I started in the mortgage industry a while ago, found that software was really up and coming and I fell in love. I fell in love with the tech industry, so I moved over, but I've been, I was in sales for the majority of my career. So I did inside sales at a tech company for a while, moved up to leadership fairly quickly, and then started leading different teams there for sales.

Moved over into marketing because I found that I wasn't quite getting what we needed. There were some things that I wanted to solve. And so I pitched the position out to the VP, set up a meeting and she said, yeah, let's go and solve it together. That sounds good. So that's how I ended up in marketing. So I didn't have a marketing background, but same thing that I did with tech is I fell in love with marketing and just the impact that you could have for the customers and also for your sales 

Nelson: team.

You said you fell in love with marketing and the impact and that there were some problems that you were trying to solve. How did you arrive at that? 

Nicole: I was leading inside sales teams and I led some inside sales teams for a while. One of the things that we weren't receiving from marketing were really, really impactful programs that we could take to our customers and then out through the channel. And everyone in marketing is so busy. So even though we asked for help, they didn't have the bandwidth to really create the programs that we specifically needed. We were going off after an audience segment that wasn't – it was part of our go-to-market strategy, but it wasn't the sexiest channel that people really wanted to go after.

So people weren't making content for it. We said, I think we could solve this. We've got the intel, right? Because we talked to the customers and our partners all day long. We know what we need and what we want. So let's just go and start producing it. So we started creating something called the "Campaign in a Box."

And it was an end-to-end journey that we would bring someone in and get them to the buying stage. So we started to do that and we started to have some really, really great success. And then there got to be this little buzz around the company that was, people were wondering what was going on in commercial or the mid-market segment at Symantec. There's all this pipeline that's getting generated and how are they doing it?

So we started to share out what we were doing and we started to teach our enterprise segment how to do this. I realized you could make a huge impact for the company by creating programs that turned into revenue. So instead of just managing one small sales team, if I can expand that out, we can start doing more for the entire company.

So that's where I took the initiative and told my boss that this is an area that I wanted to go into. Luckily I had her full support, which was great. Set up a meeting with our VP of Marketing and pitched, it said, Hey, this is what I think we can solve. And this is what we've been doing. And here are the results that we've had so far.

And the meeting went really well. She built the role, brought me on as Director of Marketing for Symantec. And I started to do mid market marketing for Symantec, which was mainly campaigns in a box. 

Nelson: That's awesome. And I think that's probably the best way to carve out your career path internally. If you present to the powers that be that there's this problem that you noticed, that you want to solve, and you took proactive action and built this campaign. I'm kind of curious, since that shift from inside sales to marketer, has that made you a better marketer? And if so, how? I think 

Nicole: it builds instant credibility with the sales team to say, Hey, I've sat in your seat.

So I understand the struggles and I know how hard it is. And I know how amazing it is when you can give the sales team a reason to make a call or send an email. It has enabled, I think, future success coming from sales, and I would highly recommend anybody that wants to get into marketing try sales first.

It is a great avenue to get into marketing.

Nelson: You relatively recently joined Reciprocity from Symantec about six months ago. Your first hundred days are not too far in the rear view mirror. I'd love to kinda hear about your first hundred days at Reciprocity. What did you focus on versus avoid? And what would your advice be to people in a similar situation as a Director of Marketing in such a company as Reciprocity? 

Nicole: I have to be transparent that I have a blueprint for success.

It's a book that's written by Michael Watkins called "The First 90 Days." Pick this book up. There's podcasts on it too, by the way. That was my blueprint. It's a proactive approach to help you develop a plan. It chunks it out in 30-day segments, which I think is about the right amount that you really need to plan for. Because let's be real, your first 30 days, you're not really even sure who does what, where, who you can go to for what? So you really need to, first and foremost, set out on your learning journey is what I found. But before you even set out on your learning journey, you need to get buy-in from your leader that that's acceptable. So hopefully you've done that prior to accepting the position where you've talked about what that 30, 60, 90, or what it looks like for you, that you have planned that out to say, Hey, I am going to go and interview just about everyone that I can and touch some within the company to understand what do they do, and what's the impact.

And then you take that information and really, you start building out, what are those goals and those milestones that we really need to start solving for? There is something to be said for finding quick wins to show your value right away. But on the other side, studies have been shown that, I think, it takes six months for someone to move from being a consumer, in a sense, to a producer.

You need to know that you can give yourself that cushion to say, you know, at six months I should know, and I should be able to start giving back to the company that has now invested in me. So that's how I plan for successes. I used the book and I really wrote out what I wanted to accomplish on each of those. The other side of it – and you asked me, what do I want to avoid? Here's my downfall, is I like to jump to conclusions too fast. So I always, in my back of my head say, don't try to solve this yet. Yeah. Let's think through first, what are the contributing factors and what do I need to know before I come up with that conclusion?

So sometimes we push ourselves to go too fast and that can be a mistake. 

Nelson: That's very interesting. And then you also touched upon something I thought was interesting, which is you have a mixture of short and long-term goals potentially, or things that are important, but not urgent. Urgent, that kind of matrix.

How do you prioritize? How do you create like a hierarchy of what to do? How do you contain all that?  

Nicole: Spreadsheets. It was a spreadsheet. It wasn't something that I shared out with everybody, but every time I found something that I would consider, that it needed to be solved, I started to populate it into a spreadsheet.

And so then I just started to categorize them. Again, part of the blueprint for success is understanding is this something that is I can do as a quick win so I can turn this around within a couple of days and everyone's going to be excited. Is it short or is it long? So quick wins were a no brainer.

Just go and do them and get them done. Short and long is something that I collaborated with my leadership team on to say, here's what I found. Here's what I think we should go after and solve quickly. And here are the long-term goals, always thinking through and in the back of my head, what is the mission and the vision for what we're supposed to be doing as an organization and making sure that those still aligned.

Nelson: Let's take things in a little bit of a different direction. So I guess looking back at your first hundred days, and you have this blueprint that has helped you. Now,, were there any mistakes that you've made looking back on that you'd want to share, like what happened and how, and what did you learn from it, and what's the takeaway from it?  

Nicole: As a startup, we move really, really fast. And I got pulled into a strategy conversation. I think I had only been there for a few weeks and I got asked to give my opinion on a pretty major decision, whether or not we should think about moving people, teams, that sort of thing together or apart.

I thought, wow, this will be fun. Like I want to jump right in and I'll use some of my past experience to give my opinion. Well, I shouldn't have done that. Let me just be transparent. I made a mistake and I gave my opinion based on my previous knowledge of a totally different company that had different, a little bit of a different mission in that sort of thing.

I had to actually go back and tell the team that I have to change my opinion and the advice that I gave on how you should be set up and structured based on what I know now of the company. So my mistake was that I jumped in too fast. I tried to solve for something based on my previous knowledge versus really understanding where the company was today and where we should be moving to.

Plus, another side of it is I should've asked my mentors, too, for help on this one because they have more expertise around that. It was really interesting to have that conversation. He asked me some really powerful questions. Changed my mind in that conversation and thought, wow, I wasn't prepared or ready to make those suggestions.

So it actually went really well when I turned around and had to have that conversation with the leadership team to say, I'm actually reversing what I told you a week ago, based on where I sit today. They were a little disappointed, but I think I built credibility with them and a lot of respect and understanding that you have to let people go through the learning journey before you put them in that position to make strategic decisions. It really set the tone for honest discussions so that they knew that I was going to be transparent. If I think I made a mistake, then I'm going to come to them. And I think that built an additional layer of trust between somebody that I was newly working with. 

Nelson: That's a really, really good point.

Own up to a mistake and build that trust. People are understanding if you make a mistake, but they're not very understanding if you make a mistake and don't want to admit it. But enough of Nicole, any mistakes, the audience wants to hear, the audience demands a success story, to leave on a positive note so can you tell us about a great victory that you had and then what would be the takeaway for the audience on it? 

Nicole: There have been a lot of quick wins and some big major successes. There was a lot of opportunity at Reciprocities. I came in to a team that is a high-functioning sustaining success team.

So that was the model. I knew I needed to take a very, very great team to even greater success. So I spent some time working on the blueprint for what that would look like and identifying the key areas that I thought could make the biggest impact and got buy-in. I have to say that's one of the key as you're making any sort of changes is socialize it and get buy-in before you go ahead and make that change. So did just that. We made a significant change between the way the sales and marketing organizations worked together in what we saw was an immediate increase for marketers on their conversion rates, right, which is really, really key for us and conversion rates equal more leads, which equals more pipeline, which equals more bookings.

That ramp up has continued to this day. So very, very excited for what we were able to put in place and the collaboration and the partnership between sales and marketing is even stronger today than it was a couple months ago. 

Nelson: So looking back on that success. Buy-in was definitely key. What other advice would you give to someone looking at that success to say, if you're in such a similar situation, in addition to getting buy-in, what would you recommend?

Nicole: You have to focus on the people side of it. The people are the ones that the change is going to impact the most. So I think that was another part of why we had such great successes. Brought the team together to say, even though we're doing very well today, here's where, based on the metrics and the data, where it could take us.

So getting them to agree on the small steps to get to the big, you know, rip the band-aid off change was really, really critical. So I would say involve more people then maybe you're even considering today. 

Nelson: Have you been surprised by people that you've involved, where you didn't think that they would have an insight into something and then all of a sudden you're like, wow, I'm really glad we brought you in. Have you ever had that experience? 

Nicole: Very much, so very much so. I learned early on that that's critical. We've done some things previously at Symantec that we're bringing to Reciprocity that I'm very excited about and something called the Innovation Lab, which is just what you had talked about.

Bringing different people from different parts of the organization together to talk about innovation. Because unique personalities and unique people bring unique ideas to the table, and we want to make sure that we are gathering as much as we can from everyone within the company. 

Nelson: I like that.

Another thing to take away there with the audience, there was a good practice you had at Symantec, this Innovation Labs, that you can bring right to a new company and say, Hey, here's what I learned. Maybe this could be interesting for us, too. How do you know when you're ready for the next step? Whatever level that you're at, at what point do you say to yourself, you know what? I think I'm ready, whether it's a new industry or a different company size, or just the next level. How should people be thinking about that?

Nicole: I think that to know when you're ready for the next step would be unique for each person. For me it's I know I'm ready when I'm not being challenged in my current position and I find something that I am more excited and maybe passionate about going out to solve. Now I'm going to dispel something real quick, because I think a lot of people think about careers as a ladder.

And for the people that I mentor, I try to explain to them that it is very rare that I've ever seen a career ever look like a ladder. Careers are more like a jungle gym. And I think someone else said that first, so I'm not going to take credit. But I would say that's been my experience as well, is that once you get on the jungle gym, sometimes it's a swing and you swing over to the next level.

Sometimes you climb up. Sometimes you crawl around it. But it's very, very rare that you just go straight up. So, there are times where you need to swing to the next position. Maybe it's lateral, but you're feeling a box that you need to get in order for you to get to your ultimate goal. And that's great.

And that's okay to have a jungle gym versus a ladder.

Trinity: The First 100 Days is sponsored by User Gems, a software that helps companies identify buyers that are more likely to buy your product. User Gems tracks your current and past customers for job movements so that when they switch companies, you can sell to them again. And based on your sales and product usage data, it also finds prospects that are similar to your existing customers.

According to reviews and G2 crowd, and I quote, "User Gems is a prospecting miracle." If you're in a revenue role, check out Are you going through a major transition within your organization or your career? Do you have a first 100 day journey to share recently or in the past? If, yes, I want to hear from you email me at

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