Top priorities for a new CMO

In the first episode of our new CMO Alliance feature, CMO Diaries, we chatted with Yoni Solomon, CMO of Uptime.com. Yoni stepped into his first CMO role just a few months ago. How has he tackled this daunting task? We discuss what he's prioritized, the big differences moving from a large-scale tech company to a start-up, building relationships with other departments, and the importance of good contractors.

You can find the full episode here, but read on for a write up of what we discussed.

Yoni's background and CMO role

Before we get down to what actually CMO Diaries is all about, could we go into your background and your role as a CMO at Uptime?

My name is Yoni Solomon, and I'm the CMO of Uptime.com, and I've spent the last 10 years at a variety of high performing B2B software companies, from Vibes to PowerReviews to most recently G2 where I lead product marketing for a couple of years, before coming over to Uptime.com a little over two months ago, to help build the marketing arm, the brand, the funnel, from the ground up for this new and exciting company.

Yoni's first two months as a CMO

So those two months, it's got to be a big learning experience and that's what we're talking about today as part of this series, it's going to be about what you're learning in your role as a CMO and what resources you're relying on.

Probably the best way to talk about it first is what are the responsibilities that you're finding, as a CMO? What are the most important things in these two months that you've been tackling?

Sure, a little bit of everything. But if I had to break it down into some product marketing pillars of the CMO role, if you will, first and foremost is building and cultivating a strong brand. And for us brand ties into two very important components.

I would say, first and foremost, it's about awareness. It's how are we building a recognizable mark, that's trusted by customers, that's known by analysts, that's picked up by media. Cultivating awareness is a big piece of that brand. I would say piece two is experience.

So within our own platform, and on our own websites, in our materials, in our comms with customers, how are we building this best in class experience for IT professionals for site reliability engineers, who really trust us to monitor the health, downtime, and performance of their websites in an accurate and reliable and elegant way.

And so when you have these two big components of building significant brand awareness and building a really polished and elegant brand experience, that's a big top priority of mine right off the bat in regards to brand.

Number two is funnel. If the brand is here to create this awareness and inbound demand for that product, we have to set up the funnel the right way to actually pull that awareness, to pull that demand in and convert it. So the way that Uptime.com functions today is we have a free 21 day trial of our web monitoring software, no credit card down, no shenanigans, no strings attached, or anything like that.

Our goal, for instance, with the funnel, working all the way back is to drive X number of new free trialists every month, and have, why don't we say 15 to 20% of those free triallists, convert into a paid subscriber, which of course equals a new plan, a new customer for us.

And so really building that funnel to maintain the growth that we've had today, while also scaling it for tomorrow, based on new personas, new geographies, really understanding what our ad content is going to be and how we're targeting that across different websites, is that in line with our messaging and positioning?

Are our landing pages ready to go to capture and convert that kind of demand? So really, brand number one, funnel number two. Number three, I would call content and product marketing.

So how are we messaging and positioning our new products or capabilities or features to the market? How are we getting in front of customers to present those? How are we benchmarking an increase in monthly average users of our product?

How are we tracking new integrations that are being connected, new upgrades that are being sold? And so between all three of those elements of brand, funnel, and then the product is where you'll find me on a day-to-day basis.

That's a lot to be taking on, especially since you've come from big tech companies where you've been had loads of resources, loads of big teams available. And now you're moving into the startup world and you're the top dog of the marketing...

The only dog.

That's got to be some big challenges that you're finding new ways to workaround.

It's interesting coming in here to a new company. G2 was anywhere between 300 to 400 people while I was there, and at its peak, my marketing team at G2 was probably close to 50 folks across the board. My product marketing team was a team of six, those are significant resources.

And it certainly made this idea of who is doing what and what results they're responsible for, much easier to manage. Whereas here, coming into a brand new company, that mind you has been up until now built solely on product, engineering, and support.

There's never been a dedicated sales and marketing focus. And so you're coming in, and sure, you're the CMO but you're also the marketing intern, you're the marketing coordinator, the marketing manager, the marketing director, all at the same time.

And so I think the things that have helped me right off the bat, not get lost in the forest, if you will, is ruthless prioritization. If you're a new marketer, coming into your first VP or CMO role, you know you're going to be taking on a lot, just know that that first and foremost strategy lives and dies with you.

And before we can start to execute anything regarding tactics, we have to absolutely understand what our marketing strategy is, and what we're trying to build, so that you can have those really transparent conversations with your CEO and with the rest of your SLT on here are the things that we're going to do - here are the things that we're not going to do right now and these are the reasons why.

And so when I got to uptime.com, those are some of the first conversations I had, I spent my first week in full on observation mode, customer calls, reading all of our review content, reading everything, and learning everything I could find about the company, understanding what our marketing tech stack was, really just getting a lay of the land.

And then at the end of my first week, I presented my recommendations on, based on what I'm seeing here, these are the holes for the business.

We absolutely have to build brand awareness, we absolutely have to bake a better customer experience into our software products, we absolutely have to find a way to grow our top of funnel, accelerate deal velocity, and also increase conversion at the same time. Then on top of that, we have to start building out our queue of product marketing launches.

That was literally my punch list with him. And there are a million other things we could be doing in the middle of all that, we just can't do it at the moment. So I'd say ruthless prioritization and clear goal-setting and expectations have been the most important piece. And then piece number two is building a really strong network of contractor relationships.

For instance, I work with an excellent contractor on the growth marketing side of things to make sure that our AdWords are perfectly tuned and are in a position to convert as much as possible. I'm working with a creative director on our rebrand, we're going to roll out an entirely new look, feel, and story around uptime.com. And then slowly but surely you start to hire for your team from there.

So I had my first FTE, full-time employee marketing associate, and hopefully have a couple of offers going out over the next few weeks to start to build the team out. But coming into that new role set your expectations loud and clear, make sure everybody knows why you're doing it, what the goals are.

And then from there, start to build those contractor relationships to give you some breathing room while you get everything else done, and then begin to hire for need first and foremost, when it comes to full time.

Priorities for a new CMO

Let's break down those two sections. So it's the prioritization and the contractor connection. Let's start with the prioritization. Not to throw anyone under the bus or anything like that but did you meet any resistance with some recommendations you were making?

Were there any hurdles you had to overcome to get buy-in on certain things that you wanted to do? Were there certain things that they wanted you to do that you said, "No, we shouldn't be doing that"?

Absolutely not. And I think it's really important to note when you're in the evaluation process trying to figure out what your next move is going to be absolutely make sure that of all the things that you look to make a choice on when jumping to a new company, the market opportunity, revenue, customers, whether you like the product or not, these are all not surface-level things, but the basic criteria that we as people always look at when we're checking out a company.

Before COVID, it was, "Hey, how cool is the office?" "Have my friends heard of the brand?" "Is this something I could show off and tell people about and feel really good about?" And all of those things are really important but when taking your first big leadership role, you have to put equal weight around leadership.

Who are you taking a bet on as far as your CEO? As far as the rest of your SLT? The board, the founders? Are these people who are going to believe in you? Are they going to believe in the function of marketing? And are they going to create an environment for you here where you are trusted, you're given the benefit of the doubt to use your best judgment in that role?

If all of the other boxes are checked, it's the right title, the right role, the company is really cool and you could show off about it, you've heard of the product but the leadership team in your gut doesn't feel like the kind leadership team you can succeed in as a marketer, I don't know if it's the right call.

And so I've actually been met with very little resistance here because I spent almost two months in several conversations with the founders, with the chairman, with the CEO two or three times before making that call.

Because I knew coming in, I'm going to be a solo act to start and if I don't have that benefit of the doubt and that trust right off the bat, I'm going to fail here. It won't be possible to succeed.

Establishing expectations is like a two-way street. Was that the most important thing when you were first starting?

Yes, trust goes both ways. I've been extremely transparent with them around the things that I can do, the things that I'm not so good at. I mean, even before coming into the role, for instance, I had a conversation with one of the members of SLT, who wanted to clarify what my marketing background was.

The first thing they went to was search and SEO and AdWords, and I needed to remind them, I know enough there to be dangerous, my background is product marketing. So we're gonna have to build this team around the things that I can do well, versus the things that I need to bring in people who are much better than me to do. So setting those expectations has certainly gone both ways.

But as a result, there's been very little sort of pushback or resistance to the things that have needed to be prioritized. And also, when building out those priority lists, make sure you're getting buy-in and alignment across the whole leadership team.

So it's not just me and the CEO in a room hashing these things out. When I put that punch list together, I vetted it against the Chief Product officer, the CEO, the CTO, the founder, and all of them chimed in so that by the time I put together my first marketing plan, there wasn't a single voice in that room that was thinking this doesn't sound right to me.

So it was a collaborative effort, then?

Yeah.

That probably means they've been less resistant because they've had their input from the beginning. It's their ideas that are on-page. So if they resist them, they're resisting their own ideas.

They've had more input on it so there shouldn't be as much pushback. And because they've had that input from the beginning and they felt like they've had a role in helping you build out your roadmap, they're emotionally invested in your success, too.

Because some of those are their ideas and their concepts, it's 'we're shared in this goal together'. That's been really important to not only hitting the ground running fast but in building really fast, deep relationships of trust with the fellow members of this leadership team.

All that, by the way, are totally global and around the world. My CEO is in Texas, I'm in New Jersey, founders are in Israel, it's hard to build that camaraderie and trust right off the bat when I've never actually been in a room with any of these people. And so that's been helpful as well.

Well, yeah, because usually, when you think about the startup environment, building those kinds of relationships sounds like it would be quite easy because if you think about it they're all in a pod together, working together in a shared workspace and you've got that time to actually build that trust up.

But it must be extra difficult in a remote situation. What steps did you take to build those relationships? Was it just jumping on a Zoom call and talking to them or have you had further activities to build that trust?

Yeah, it's been a lot of Zoom calls and finding the time both in terms of putting meetings on the block, knowing that there could be some times an entire day when you're not going to see them. So finding that time right off the bat to get in front of them with scheduled calls. And then also impromptu.

Especially at the SLT level, there are people who love to hop on impromptu Slack calls to brainstorm all the time and almost digitally recreate that whiteboard moment that you don't have when you're not in person.

But as much face time as possible, as many ideas sharings as possible. And also just coming in with very little defensiveness over what I think needs to be done, especially as a new marketer if you're coming in, in a CMO or VP, or even a product marketing role, you're gonna be working so cross-functionally.

My job is to make sure that our head of sales is successful, our head of product is successful, and that the marketing team is successful. And so building that cross-functional relationship with everyone to show them that you're not coming in to say, "this is what we need to do".

Rather, let's spend our first few weeks here just learning about each and every one of you, and what are your goals? What are your problems? What does success look like? And then let's find some opportunities for me to help you and vice versa.

Was that a big difference coming from the big tech world to the startup environment: those close relationships with different departments. Is that something you developed as part of your career path already?

It's gotten easier to develop those with every company that I've been at. But certainly with the larger companies, and in G2 when I was there at its peak, it was pushing 500 people, it was close, it's just harder to get to know everyone and there are so many more layers through the organization that building those close relationships with leadership just takes time and it takes schedules until you're finally in enough meetings with them that you start to build that trust and camaraderie.

And I think the biggest difference certainly between G2 and uptime.com, which really are polar ends of the spectrum, G2 just raised their series B, $1.1 billion valuation, lots of resources, lots of energy there, and uptime is really just starting to get up and running, started to hit its momentum.

We've got 1,200 customers and counting, millions in revenue, 100% year over year, but I think we're on the up and up versus something like G2 where you walk in and much of the rocket ship's built already.

And so the interesting parallel that I drew to my experience at G2 versus uptime.com, is when I got to G2, despite it being at that point post series C, lots of resources, big marketing team, the product marketing function hadn't really been built out yet.

And so I viewed it as coming in as an intrapreneur and building this startup team within this larger startup. And a lot of those characteristics do come over to uptime where I'm now just building the whole thing from the ground up.

But the relationship piece at G2 took a little longer to build, just from the fact that there were more people there and more layers to the organization. The ideas that I was bringing forward were to try to help build really add on to this machine, rather than working on the very basic components and parts at uptime.com.

Working with contractors

So segueing into the next category, the contractors, do you think this ability to come in as the outsider to build systems that weren't present gave you an ability to work well with contractors in a better way, be able to define objectives and goals for contractors in a clear way?

Here's what's interesting, before coming to uptime.com, I've never really worked with contractors before, I'd been at companies that had FTE marketing teams, and that was what I knew. And so when I was at a previous company, and we had a growth problem, it never would have occurred to me to go find a growth agency or growth consultant or contractor, we would have put out a job description and looked to hire someone FTE.

And so when I got to uptime.com, I didn't know what that relationship would be like. And I've gotta say, it has been such an awesome experience working with my contractors in growth and creative and soon to be search.

The differences between them and FTE, really, the only one is that they're just not in the company all hands. But these are people who are very invested in your success. If you're finding the right contractors, you're building a very personal relationship with them.

I meet with mine at least once a week, just like I would with any regular full-time employee. And a lot of the day-to-day nuance of how was your day? That stuff doesn't always make its way through because you don't have nearly as much time with them as you would like.

But the focus on results, I think, is two or threefold what I was used to versus FTEs because for really these contractors, it has to be about the numbers, it has to be about performance. There isn't as much time to really bake in development plans and growth, they are dead set and focused on those results and they bring a different passion and energy.

But it's been nothing short of phenomenal and the investment that my contractors have had in our business has been every bit as passionate and powerful as what I would expect from an FTE.

Did you have these strict objectives in mind when you approached the contractors, or when you put out the call for contractors, did you have these in mind? Or was it part of the conversations you had with the contractors to develop the objectives? Did they come in almost like a consultancy role to say, this is what we could do? Or was it you defining the objectives?

I think it depends on the contractor. For our growth contractor, we immediately get down to the funnel, these are exactly how many free trials our business needs to drive every month that convert at X percent in order to hit our revenue and new customer acquisition goals for the month. And so really, that was the level set of this is the goal.

And then for me, I'm taking a step back at that point to let them be that consultant and tell me 'here are the campaigns and channels that we need to roll out and the spend that we should be allocating to get to that number with this CAC', you know what I mean?

And so the baseline is the metrics, but from there I do want them to bring their expertise and input in because this is what they live and breathe every day.

So I'd say with our growth and funnel contractor, it's a little bit more related to numbers, whereas, with the brand, I just set a goal of "Hey, we need to rebrand the company. We have a new messaging and positioning story that I've worked on, but the brand, the logo, the design system, the mark, all of that is on the table, this is who we are now take that and make something cool and unique with it".

Again, it's not me telling this person what to do, it's me laying down here's who we are, this is where we'd like to go in terms of direction, now come in and consultant and help us get there and definitely empower those contractors to do that, to really invest the emotional and intellectual time in your business, rather than just doing exactly what you tell them to do.

You said you've been really fortunate with how passionate and invested they've been, was that something you were looking for when it came to choosing the right contractor? Or is it just happenstance, and now that's going to be something you look for in future collaboration?

I look for it right off the bat. Immediately, what I want to see is, is this going to be a relationship where I'm driving most of it, I'm coming forward with the projects and coming forward with the recommendations? If things are going wrong, I'm catching those, if there are things that I'm not doing right, on my end, I have to catch those myself.

Or is this going to be someone who has longevity at all their contract relationships, has a strong portfolio? Whether that's growth or brand, SEO, or whatever it is, demonstrated success of working with other businesses, and isn't here to do exactly what I tell them to do.

They're here to give this business what we need. And that includes calling me out or asking me for things when they're not getting that from me. Those are the characteristics I look for in a great contract relationship.

Is that any different than what you'd look for from a full-time employee at the end of the day?

No, and that's, I think, what's been such a pleasant surprise about this contractor relationship ecosystem that we've got going here. I'm seeing that same level of investment and thoughtfulness in the work that you would expect from an FTE.

And I expect that trend... now we're seeing so many successful full-time SaaS employees across a variety of different spaces go into the consultancy range, and take their skills and apply them over and start to work with their own book of business. I would expect this, it's really our version of the professional gig economy, if you will, to continue to grow in the next few years as more startups grow and scale and exit.

And that opens up new opportunities for talent to go in and apply that talent in a really unique way that's not linear and is tied to an FTE role as it was maybe 10-20 years ago.

There's been a bit of a misconception about freelancers and contractors that they're sort of like mercenaries...

Marketing for hire, I completely agree and I want to smash that because it's so not true. They're talented, they're thoughtful, the work that they put forth is amazing. If you are a new marketer, CMO or VP coming into a role, it's gonna take you time to figure out which FTEs you to hire for first, you're going to have to build those JDs, you're going to have to get budgets and everything approved by your SLT before you move forward.

And then you need to find candidates. And if you're looking at the moment of time we're in now, it is brutal out there for anyone trying to hire. But especially in SaaS marketing it's tough, people are not leaving, they're choosing jobs for a variety of different reasons.

And so you're also going to have to just give yourself 3/6/9 months before you find that one employee that you're 100% sure you're pulling the trigger on, but in the meantime, you're gonna have to launch you're gonna have to get stuff built. And so that's where finding those great contractors is gonna be critically important to your success right off the bat.

Starting your full time marketing team

You've got your first FTE under you now, you're not just a marketing team of one anymore.

Yeah, we've doubled.

That's huge growth.

100%, month over month growth.

So is that the priority next, building the team up? Or are you satisfied with working with the contractors for now and you're just gonna keep going until you need the team members?

There are two schools of thought that I've come across in my career in regards to building out your team as a CMO. For starters, is like let's stack ourselves with FTE's immediately, let's find the talent out there, especially if it's an unusually brutal market for talent, if you can find those people that are A+, there's no doubt we're pulling the trigger, let's bring them in.

And even if we're not sure what we're going to do with them yet, let's get the talent into the house and they will start to figure things out. And then there's the other side of things where you hire incrementally based on results.

I tend to go with the second route. That was honestly indicative of my time at G2 as well, where we started, it was me and we had a product marketing associate who had been a longtime employee of G2, who had moved in from a client success to sales enablement to a product marketing role.

So I was just starting at G2, she was still starting out in product marketing and we started there to see what we can build. And as our results grew, as we started to harden our ROI, as we started to decide what we were going to track and metric, we started to blow those numbers out of the water, we started to hire incrementally from there for another member, another member.

And then finally another two members. I would like to take the same approach here at uptime.com, I think, for now, I see our metrics and our projects going in the right way, I see really strong contractors who continue to give us that same level of thoughtfulness and expertise that we need from an FTE.

And if I had to choose a certain way to go, it would be let's continue to set metrics, blow them out of the water, and hire and grow incrementally so that we're constantly proving back ROI to our headcount. And it also relieves some of the pressure and risk of just trying to hire fast, or perhaps pulling the trigger on the wrong people.

My old CMO from G2 always used to say you shouldn't hire anybody unless you are desperately sure that you couldn't live without them. That level in your gut of “I absolutely need this person”. If it's anything short of that, don't pull the trigger. And it's been a very important lesson I've taken with me

A good quote in in relation to that is something like "better a hole in the team than an asshole on the team".

Ha! I've not heard that one. But yeah, it's the worst thing you could do is rush that hire, pull the trigger, and miss.

There's more chance of that if you're just building a team completely from scratch, and throwing all these different personalities into the mix at once, there's more chance they're not going to fit together, they're not going to have the right personality fit to work together well as a team. Whereas if you're doing it incrementally, you can think about, is this person going to work well with my current hires? And then build it up like that.

Exactly right. And you start to build for system fit. So with every new hire that comes in, you, as a CMO are saying, "Okay, I've got growth in a really good spot. Now I've got design in a really good spot. Now what do I need next?", versus bringing people in a little bit too quickly, and having them bump into each other, not sure what everyone’s superpower or roles and responsibilities are going to be.

And also, it's a much easier story to tell to your SLT and to your board, when you're hiring based on growth, and based on demonstrated success. It's like, as soon as we've hit this ceiling of, “we cannot take on one more project or drive one more dollar in revenue until we bring in another head”, that's when you know it's time to hire.

When it came to the prioritization, was working with contractors a conversation you had then? Was that something that was established as part of the initial priorities for the business?

Yes, it was and on the growth side, they've been working with the growth contractor. And so it wasn't something new. I have to think that in, I think uptime was started around 2013 and I have to imagine that since then, they've worked with contractors for design projects for maybe a website launch.

And so that wasn't necessarily going to be a foreign concept for them. For instance, when I came forward and said, "Hey, we're going to go through with this rebrand. Not only do we not have an FTE designer or brand manager, but I want to work with a contractor for this." it was a very easy conversation to have.

And so I don't think there was a whole lot of framing I needed to do with them, because right up front before I got to the company, they knew I wasn't a designer, they knew I was a product marketer. My superpower was going to be messaging and positioning. But we need someone to build the visual layer on top of that new story.

And so again, it all comes back to setting those expectations right off the bat so there are never any surprises when you're sitting with your SLT and they're like, what do you mean you're not going to design the logo yourself?

You've got to be honest about your weaknesses otherwise the house of cards quickly falls apart.

These are the things I can do. These are the things that we need to build out a strong contractor ecosystem for. And everything that I can do on my end is going to be providing them the day-to-day management, the strategy, I'm checking a lot of the work, we're now working with a PR and media agency in the same way.

I'm going to be there in the middle of all of it, but you are going to need those hands if you have any hope of scaling a full B2B marketing function within a SaaS company. It's not a one-person job.

Choosing the right contractors

Let's talk practicalities when it comes to finding the right contractors, what were the best resources for you? Where did you look? Did you have a recruitment agency or were you doing all the search yourself? How did you go about the process?

For growth I was lucky that I inherited our growth marketing contractor, he'd been working with the company for some time. But the things that I look for in contractors right off the bat are gonna be personal relationships. Do they come recommended or have I worked with them before?

And so for our growth contractor, he's had a long relationship with the founders of the company, who've worked with him at other startups as well. And so right off the bat, there is this element of trust that he knows our people, he knows our business, he's invested in our success.

From there, it was a very natural move into the role for me, I think, in fact, he might have been the happiest person that there was finally a dedicated marketer at this company that he could sit down and have real one on ones with and put real strategy sessions down with. But in regards to the other contractors, there are two things I look for. One is going to be those personal relationships.

So the creative director who I brought in for our rebrand is someone I've known for many years, her portfolio is outstanding; Nike, Adidas, Amazon, she's worked with these incredible brands, a demonstrated portfolio of success, and I trust her a lot. And so having that sort of rapport right off the bat is gonna be really important for you as a new CMO.

So finding people that hopefully you've worked with before, you have some sort of personal relationship with because you are going to have to have total unequivocal trust with this person because there's not enough of you to go around to start to build those relationships right off the bat because you have to start launching and working immediately.

And then the second piece is actually reviews, coming from G2 I'm always thinking through, where can I find UGC? Where can I find user-generated content and social proof that these businesses work?

But that was integral in me picking out our PR and media contract agency, the first thing I did was I went to reviews and I looked to see what people were saying about them.

And so in the absence of those personal relationships, go online, read reviews, reach out to customers that they have on their website, gut-check those relationships before you pull the trigger. Because much like FTEs, there's not enough time and there's not enough of you to go around to miss on those contract hires either.

Every time you miss, you have to go back to the drawing board, tacking on at least another month until you find someone, go through contracts and everything. There's very little room for error. So pull those triggers correctly right off the bat through personal relationships, and through vetting of reviews and any sort of proof you can find on their business.

5 lessons learned from stepping into a new CMO role

What are the five main lessons learned in your first couple of months as a CMO?

Five top lessons learned in these first few months of CMO. Make your decision to join a company based on how well you can work with this leadership team. Is this a CEO and a founding team that believes in marketing and trusts you and is going to set you up for success? Make that call on leadership as much as you do on everything else.

Number two set inescapably clear expectations with your leadership team and with the rest of your company right off the bat on the things that you do very well and the things that you are going to need additional help with in order to scale properly.

Three is to prioritize ruthlessly based on those expectations that you're setting. When you build your plan be very clear in saying that these are the things that are the greatest areas of need for the business and here are the things the whole list of them.

User conferences and advisory boards and Superbowl commercials - all of this stuff is going to have to wait for the time being so that we can build the house the right way the first time.

I would say number four is upon coming into the organization, take that first one to two weeks, and do nothing but listen. Join customer calls, listen to recordings, read reviews, meet every member of the team, and ask them what they're doing, what their role is, what success looks like and what the problems they have are.

And before you make any judgments on what you're going to bring to this business learn what it really needs the first time around.

And then five, last but not least, build relationships early with your senior leadership team, with the rest of your full-time employees, and with your contractors.

Those personal relationships are built on trust, authenticity, on clear expectations. And that level of trust, both with your company and with the contracts you work on just outside of it is going to make or break those first six months of your role as CMO.

Are you a new CMO in need of advice? Maybe you've got some wisdom to share from your own experiences. Head to the CMO Alliance Community.