Sharing experience, insights and best practices for building SaaS businesses. Clients rely on us to realize the future visions of their organizations. Posts here are based on real-world outcomes and lessons learned from putting marketing to work – marketing that grows software companies like yours.  Let’s build something bigger, together.

Filter by Category

SaaS Backwards Episode 20: The Perils of Being a One-Woman Army (Marketing is a Team Sport)

Welcome to episode twenty of the SaaS Backwards podcast, where we interview CEOs and CMOs of fast-growing SaaS firms to reveal what they are doing that's working, and lessons learned from things that didn't work as planned. 

You can listen to the full episode directly below via Spotify, or visit SaaS Backwards on Buzzsprout or wherever you listen to podcasts.


The Perils of Being a One-Woman Army (Marketing is a Team Sport).

Jennifer MacIver Edwards

Edited for clarity and readability 

Host, Ken Lempit:
Welcome everyone to SaaS Backwards. It's a podcast that helps SaaS CEOs and CMOs to accelerate revenue and improve profitability. Our guest today is Jennifer MacIver Edwards. She's been an Agency client a few times and we've worked on a number of SaaS clients together. Hey Jenn, before we get started, tell our audience a little bit about yourself.

Thanks for having me on, Ken. It's great to be here with you today. As Ken said, I'm Jennifer MacIver Edwards. I am a marketing leader guided by customer experience principles. Ken will tell you that sometimes we refer to me as a one-woman army.

I am also a co-founder of a nonprofit community art collaborative, and we create art that is crowdsourced from the community. It's a passion of mine on the side and it definitely helps me in my work. I think creativity and innovation are quite important these days, as we all work through the continued challenges that we see.

I think some good advice I got from a consultant in my business a while back was to work your work and then have your life. And it's important that we have a balance and that we get to charge our batteries with things that matter to us personally.

I agree. I think that should be one of our first points that we make in this conversation, having a big fat life and leading organizations, especially young growing organizations that are in the SaaS space. Having that balance is super important. And it certainly it gives you a lot more to draw on when you sometimes do find yourself short of resources and you do need to be creative. It's good advice.

Hey, so we do have a special episode planned today. It's part career advice and part survival guide for people who find themselves alone as the sole marketing resource at their companies.

We have come to call this “the one-woman army” because it's not uncommon that these folks are women. And they also work in an environment where they might be the only woman in the C-suite, which we've gone through a couple of times together.

Why is this so common out there? Why is it so appealing?

I think it happens in organizations that are at a certain point where they've had some level of success. I've gone into companies that are $500 million and publicly traded and have said, "Well, we've never really needed marketing and now it’s like the cheese moved and we need this. But we're really not necessarily super believers in it."

And someone like me... I think, one of the biggest challenges marketer space and one piece of advice, so quick career advice, really look at both the opportunity, don't just dive right into the work and the culture in the organization that you're walking into. And that's going to help you really understand where the organization is and what their ability to move quickly and break glass and move forward will be, or their inability.

When you enter into these organizations, you have to meet them where they are. Many times what's happening for them is they've hit an inflection point--it's not always because it's a disaster--they've been very successful most of the time and they're really trying to take the business to the next level. That means that there's a lot of change going on in the business, they have investment and they decide that they're going to bring a very senior leader in.

And sometimes they don't have the infrastructure underneath, and then you get to where we find ourselves in the one-woman army.

Maybe you have some junior resources and you're pulling in agencies and you're creating the round forces as you go, but that is where it comes from, I think, a lot of times, in inflection points.

I think you have smaller organizations that get an investment and they've made commitments to grow, and so they're going to need to move beyond founder-led sales. So they find someone in marketing to invest the responsibility for creating opportunity, but maybe they've never done it before. A lot of these companies, this might be his or her first startup. They think that they're going to hire marketing and that's going to solve for it.

Yes. So when they choose to do things like that, they do see it as a panacea. And a lot of times, the first thing they're thinking of is revenue generation, when they really should look at both brand revenue and engagement – they need to look at it across the experience.

That can be a really hard concept for young companies to get their heads around. A lot of times we want to just focus on the revenue, but you need to both bring it in and hold onto it.

So, what does the right level of support from a marketing standpoint, does sales and a customer success need to look like in that space? Because you'll find yourself treading water if you don't.

Then we see more pressure being placed on the acquisition. So you really want to ask the questions around how are we, not only bringing in revenue to the organization, but ensuring that it is not exiting out inside of the organization as well.

It would be nice to hold onto it.

Yes. I think that's important. And so you also really want to try to be targeted and ask questions with the organization around what they're trying to achieve. What are your one-year and two-year objectives and take them on a journey, but break it down into bite sized chunks. I like to get the big picture and then you've got to shrink it down and make it achievable. A lot of times what's being asked is likely not achievable and you really need to understand the Genesis of your organization.

If you have a CEO that's like, "Shoot for the moon and hit the stars", then you're going to be okay.
If you have someone who is a very financially driven, wants to understand every single piece and is expecting a return at the first crank, then you have a very different challenge in front of you.
And I think understanding whether you've got a north star or very financially driven (neither of which is wrong) they've gotten to the point they've gotten to. And also understanding, is there a level of self-awareness within the organization about how they're going to grow and move forward? You do have to start really dig into.

I think this is a career advice section here. It's before you find yourself in the job you have to interview for the job. I think in the wake of the great resignation, there's a lot of opportunity out there for late mid-career marketing people.

I think it's fair to interview the interviewer and really make sure you have a shared understanding of these particular issues.

I love the way you frame the leadership styles. You know, the shoot for the moon hit the stars kind of person or the person that's going to be looking for weekly dashboard KPIs. Those are different leaders. And I think also another dynamic or another access on this is the time to accomplishment.

I created an expression for CEOs that want to bend time called before now or sooner. And there definitely are people that hire you and expect that last quarter you're going to have changed results.

I think expectations setting there as well, what can be achieved in what kind of timeframe? Super important.

Not enough people ask those questions before they find themselves in the jobs. And I think it's a supportive job market, so let's ask good questions and have an agreement place that you can live up to as a marketing leader.

Marketing leaders, look, we're all individuals and whatnot, but one thing I've learned in my journey is that I get really enamored with the challenge. And so certainly, these questions are questions even as I go and start to interview clients. And in my work, I'm really looking at that because this is the difference and what's going to make you successful.I've had a number of conversations with other people that are doing fractional CMO work, things of that nature. And for some companies, it might make better sense to have someone that's very senior and they're advising and they're setting the structure because it's going to fit the business. And then they dip back in and out and they advise so that the business can grow more effectively and it's ready for it and it has a minute to mature and stay focused and not feel overwhelmed by what is being proposed.

So instead of the one-leadership hire, hire somebody part-time, the fractional CMO, you get the impact of that role, but then you put a couple of doers in to actually take the recommendations and run with them rather than expecting a senior marketer to be running the email service provider?

There's definitely a lot of that, where we see folks with 20 or 30 years of experience driving the emails, makes no sense.

Then you'll find turnover where you don't want it. So if you can find the balance of someone that can set strategy, work on execution, help write those job descriptions, help you source those people, get them situated, bring in agency, help you build out the budget that you need and waterfall, and really think through that and then dip in and out. And, of course, the strategy piece of it. You do have your messaging and your positioning and all of that as well-- it's very important. And so these things all cost money, and we all know that budgets go pretty quickly. So how do you maximize your effectiveness. That especially like goes for when you get that CEO that's very financially oriented and there is an expectation around metrics and reality versus the myth.

But I like the idea though, if you have a conversation with a CEO on the way in, it's like, “Hey, if you've got a $250 or $300,000 budget for people in, do you invest that in one person? Or do you invest that in three people, one of whom is working quarter time for you and making those other people very productive. I think that's an interesting conversation for people who are flexible in what they are looking for, to have with potential employers.

But, let's say that you didn't have that conversation and you're not interested in being a fractional CMO.

You got to dive in.

So now you're there you find yourself, it's week one and you have goals to meet last quarter and it's just you and other than heading for the Hills and trying to find another gig, what are some good survival strategies for the one-woman army? In other words, what do you do to survive in the short term and build an organizational approach to investing in marketing intermediate term.

Look for the low hanging fruit, where you can make a visible impact to start. That’s absolutely important to do.

So, in a lot of cases that might be looking and seeing what they've already actually successfully been able to do, looking at that pipeline, understanding where they're headed, go see if there are any opportunities to either participate in thought leadership, get the organization out there, do some webinars, some small things that are actually going to get you on the board, but that start to move you toward their goals.

Those particular goals will be more towards lead generation. If for some reason they are more oriented towards the brand piece or analysts than look for those. Have they set up their relationships? Do they need to do that? Get them moving. Get those pinned down. You got to pick one or two, maybe three at the most. Do specify that you need 30 days to go through and dig through things. If you literally got nothing, then my recommendation is hopefully by this point you have frames of references and frameworks and learnings that you have from the past, begin to start to understand those, get your marketing automation in place, think through the budget that you're going to put in place. Look for the early-term beginnings of revenue, what your MarTech stack needs to look like and content. And look for content within.

And don't count out your data scientists, your tech, your this, that, the other thing. All those people when harnessed the right way can be great content creators--just having a dialogue can create content. So you have, probably, a lot in front of you, but you're going to want to set your buckets up. So brand content and demand, operational excellence and then engagement, which is sort of that longer piece. And look to understand how in each one of those you put your two or three things you're going to do, and then look for your short term wins. And then communicate, communicate. What do they say?

The mantra is, "Tell them what you're going to tell them. Tell them. And then tell them again." If you set those expectations early and you hit them, what we're trying to do here in this phase, first 60, 90 days of your engagement, as a new marketing leader is build credibility for the function. And then when you learn enough about what the dynamics really are, build the investment case for building out marketing, if it's not properly funded.

So let’s say you're making your six-figure salary and they give you $60,000 to play with for advertising and another $50K of other discretionary bucks, besides your trade show budget. In other words, you're woefully underfunded, what do you do?

The first thing you do is before you go in is to ask what the funding for marketing is.

It should be between 5% to 10%.

The other thing I'm going to say is to check out Austin Lawrence Group’s “New Marketing Leader’s 100-Day Plan.” That will give you all the things that you should be thinking about as a new head of marketing--sometimes I go back and look at it and say, what did I miss here?

A lot of times you're moving a million miles an hour and you need to stop and refresh by looking at other things or just caring for yourself. It’s going to make you more effective at what you're bringing to the table.

It is important that the work that I do for the community, our collaborative, has made me a better professional. It's made me better at a lot of things, frankly. But I used to just cram 15-hour days, and that was about it.

I totally get it. And I’m wondering how I can use these ideas with some of my other clients?

I just think you must be open to what things outside of your work can do to help the rest of your life. There is a real cost pollination.

I want to go back to the one-woman army, so you're in there, you've done your first 30 days or 15 days and you're come to realize that you need help.

And you don't have a budget to hire but you have, hopefully, a Rolodex.

One of the things I've noticed about working with you is that you bring some of your experts in: you have a content creation agency, you have an SEO firm, you have a syndication resource, you have things you bring in.

So to me, as a partner, what that says to me is you're not going to allow the lack of hire to get in the way of doing the job. You're going to get the position players on the field, whether they're employees or partners or vendors.

Can you talk a little bit about your thought process around that? And how you found these people? And if his is your first go, how do you do that? You've been a marketing manager somewhere now you're the head of marketing and you're solo.

Networking, is one of the most important things you can do. If you're in-house right now and your mid-career and you've got some great leaders that you've worked for and with, most likely, their networks span in an interesting way, people branch off and start doing, as we get more senior and move through our lives, we do different things.

The marketers that I think are most successful are also social engineers in that they like to talk to people and they can see things differently and they build a team.

A lot of times I will go in and they're like, "We want a unicorn the farts glitter!"

And I'm like, oh my God, marketing is like made up of all these, it's a function with a million little disciplines.

So there is no utility player--everybody's specialty. And they're really, a lot of times, even further now, very deep in it. So how do you build that out?

Part of it is if you're in inside and you're insulated, then please make sure that you reach out and you just start having conversations and you stay aware, and you'd be amazed.

You can reach out to people, and they'll just help you out.

A lot of the people that I do business with are people, along the way in my career, I've either met or I've gone, and I've said, "I have this need, can you help me?" Or I've worked with them and then they've decided to branch out on their own. For example, I have a fantastic SEO firm, someone that I worked with, she has got her own thing. She's brilliant and very, very sharp about that piece of it.

At Ripcord, I did a lot of work for them as a consultant. And my leader had brought in both a great organization that did branding, graphics work and also a content leader. And I was really happy with their work, they were very good price point and great writers and able to turn things and really get things situated accordingly.

And then of course we have the work that you do, Ken, and the team. And that, really, we've integrated a number of Salesforce and HubSpot and we've pulled in Zoom and a bunch of other different piece parts and built all of that out and developed a lot of different things. We've also worked ABM.

So it's about your social network. It's about reaching out, even if you don't know people. If you see something that's really interesting and you want to just take 15 minutes to learn more, most people are flattered and willing to have the conversation.

And I would also say, if it's your first time, then don't hesitate to go to either your former leaders that you feel comfortable with or find an agency and let them help you.

So I think you have to be willing to ask for help, as alone as you feel, you're not actually alone.

No, you are not alone.

If you have a partner that has one discipline, like a PR firm, they might very well know an ad firm that could help you to do a paid strategy.


And so you can build your team through referrals. And realize some of these folks may have some vested interest in those referrals and that's fair game. Obviously, the tech vendors want you to buy tech. But in the end, I think you can put together a team of complimentary skill sets on an outsource basis.
And I think also expose that to your CEO and say, "Hey, we're going to start here and as we build our credibility with you, we're going to in-source some of these functions to whatever extent makes sense and build our organization." I think most CEOs are pretty comfortable saying, "Hey, if we don't like the world, we can undo the vendor relationships a lot easier than the full time hire."

And seasonally, you can move things up and down and you can do the same with your spend when it comes to media and other things, which can be really important and a smart way to kind of look at it. Everything's seasonal, your events are seasonal, your media spend ends up somewhat being seasonal to some degree. And so you can effectively plan and give them a very detailed orientation around that. And from there, you can build the waterfall.

The hardest part with them is helping everybody understand that this is not a straight line. And there are a lot of different activities that are going to go to help bring that sale to fruition and the timing and everything else. That's a whole other factor that you do need to, especially if you are being asked to really focus on revenue is to make sure you understand the time to close as well.

If it's a nine-month sale, you're a year and a half away from changing it again, right?

Yes. And you're a sales leader, right? So going back, again, career advice, ask to interview your sales partner--they're your partner. And do ensure that you are partners in this approach, that it is a partnership. The best ones that are the most effective are partnership.

I think that's really interesting advice, the idea of meeting with the sales leader, if you're coming in as marketing leader. I've heard people talk about being interviewed six, eight times or more, pretty grueling interview schedule. And I think you have to make sure that that includes the sales partner.

And don't be afraid to flip the script, you've got to be willing to interview them.

Healthy relationships have some parody. Now, obviously, you work for someone as an employer/employee relationship but there is some parody and some peer to peer aspect. We're all adults, so there is a peer to peer aspect of it. And part of that is suitability of the organization and the other people that are seated to your own success and your own mental health.

Culture eats strategy for breakfast.

We spend a lot of time and energy in the workplace with people and both parties want it to be the right fit. I guess now, speaking to the CEO side of things, hey, that's why you make sure you're asking these questions too. You want to make sure that this is the right fit for you, you're totally invested in this, especially if you are young and founder-led a company, you've got a lot on the line and maybe you've taken your first round. So the chemistry is important. The outcomes are important as well. But so is the work-life balance.

Chemistry from the CEO's perspective is a good point. You have to like the personality, not necessarily the person, but the personality has to work for you. And you bring up a really good point. The other side of the one-woman or one-man army is the CEOs putting all their eggs in one basket. So you better make sure that that relationship works for you, as the CEO, the founder of these smaller firms.

I think we've covered a lot of ground here. It's be smart on the way in, make sure that you understand what it is you're getting into. And I think, you're right, the problem is really interesting but that's not what you're going to actually live with, you're going to live in the job and the organization. But, solving the problem, that's what we do. We all have intellectual fun here is solving problems. If you were going to give one bit of advice to your younger self, looking at some of these one-woman jobs you've had, what would that piece of advice be?

It would really be about separating the building or the fixing, or whatever it is, from the organization and understanding where the organization is so that you can be most successful with it. That would be the advice. Understand where your organization is so that you can be successful together. Make sure your definition of success is aligned.

That's great. Hey Jenn, I think that's a great way to sum it up. And I really appreciate you sharing time with the listeners of SaaS Backwards. If potential employers or people want to get your advice, want to reach you, what's the best way for folks to get you?

Oh, they can reach you and you know where to find me. You know that.

Oh, nice.

I will say you can also find me on Instagram. I encourage you all the checkout, our art and the work that we're doing there. And I am the woman behind the DM on that.

Thanks for listening to the SaaS Backwards podcast brought to you by Austin Lawrence Group. We are a growth marketing agency that helps SaaS firms reduce churn, accelerate sales, and generate demand. Learn more about us at You can email Ken Lempit at about any SaaS marketing or customer retention subject. We hope you'll subscribe, and thanks again for listening.

Write a Comment

New Call-to-action