A big hello from Raleigh, North Carolina and welcome to another episode of B2B Marketing & More.

Today I have a special guest – Kayla Graham. Kayla is the Operations Manager, wears multiple hats and is responsible for a company called Content Callout. She also does a lot of day-to-day internal operations, covering external-facing operations at the same time.

Our key focus in this episode is on startups, marketing and sales alignment, and how to optimize it for startup companies.

In this episode:

    • Who should startups with limited budgets decide who to hire first?
    • When building a marketing team, is it better to outsource or have it in-house?
    • How to build brand awareness with a limited budget?
    • What are the must-have tools for marketing and sales to achieve business goals?
    • What makes marketing and sales alignment difficult in a startup?
    • How can marketing and sales achieve long-term collaboration or process?
    • How to plan, prioritize and de-prioritize tasks?
    • What are the most common sales and marketing alignment challenges, and how should startups address them?
    • How to integrate necessary tools?

Quotes from the episode:

“When we’re doing B2B, people don’t want to connect with the machine. They still want to connect with a story. Yes, they want a solution that works. Still, ultimately they want to connect with the story behind that and the authenticity. ”

“I think that marketing, especially in a small company, is split up over so many tasks that it becomes hard to support their own internal sales team when a lot of their efforts are focused on external factors.”


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To expand your knowledge about marketing and sales alignment for startups, check out some of my previous podcast episodes, blog posts, and video.

Podcast episodes

Growth Hack Strategies For Your Startup

Content Marketing Strategy for Startups

With Buyers in Control Sales and Marketing Must Align

Blog post

How Marketing Can Support Sales in a Changing Environment

Sales Enablement: How To Boost Your Communication with Sales in 6 Easy Steps


How To Facilitate Sales and Marketing Integration within a Large Enterprise


Pam Didner: Big hello from Raleigh, North Carolina. Welcome to another episode of B2B Marketing & More. We are talking about our favorite topics today: B2B marketing. Our key focus for today is about startups and the marketing and sales alignment and how to optimize it for the startup companies. And I have a special guest, Kayla Graham. She is the Operations Manager, but she wears multiple hats and is responsible for a company called Content Callout. And she does a lot of day-to-day internal operations, but she’s also external-facing at the same time. And she takes care of her clients’ SEO content marketing outreach and all sorts of marketing efforts. So we will talk to her a little bit more about this.

Welcome, Kayla.

 Kayla Graham: Hey Pam. Happy to be here. Thank you for having me.

Pam Didner: Oh, any time! So, you wear multiple hats, and I assume the company is also in the growing stage. You are not working just for the company Content Callout, which is a growing company in the ways of the startup itself. You also work very closely with many of your clients, who are SaaS-based platform companies. And you probably have a very specific point of view in trends of when the company was formed or to start up just started. With the limited budget, they need to determine whom they should hire. Should they hire a salesperson? Should they hire a marketing person, or should they get an operation person to set up a process? What is your thought in terms of what should they hire first?

Kayla Graham: Ah, yes, you have hit the nail on the head here of basically the chicken-egg situation, and also, as you mentioned, startups don’t have a lot of money. So I think there are kind of two ways to answer this. And I’m going to back up the bus here and take it to the beginning, which this might seem obvious. But before you even start with your operations and your sales team and your marketing, are you ready to sell yet? So let’s take a look at the tech.

Pam Didner: Awesome, awesome. I love that question!

Kayla Graham: Because, first and foremost–and this has happened with, with a company that I was working with–you know, they, they went to market, they were ready to go. They had marketing, sales, operations, and business, but when it came down to brass tacks, their tech wasn’t ready. They couldn’t deliver on the features they said they were doing. So, I mean, we will assume that that’s in place. We have all of that.

Pam Didner: Bottom line is you need to make sure your product is ready.

Kayla Graham: A hundred per cent. And you know, a lot of the times we’re working with companies with seed funding, but they might not have Series A; and to get to that Series A, they are like trying to get revenue. They’re trying to get the product on the market. And sometimes like, quite frankly, it’s just not ready. So assuming that we have all of that in place, everything’s ready to go.

The next thing that happens is that CEOs do everything at first–they’re their admin and their own sales team. They’re their own ops team marketing, all of it. So, when it comes down to hiring an employee. Number one, I think CEOs are often like, “well, I need someone in sales. I need to sell, sell, sell,” or they might hire an operations person instead. And I think it comes down to is “what is your strength as a CEO?” So if you’re very, very process-focused, you probably actually want to go with sales first. Maybe you’re not that good at taking those calls and doing that outreach. I mean, it can be very soul-sucking take meeting after meeting, after meeting and just hear the word no over and over and over again, you know?

But on the other hand, if you aren’t very good at operations and don’t know how to make a process and don’t have them, I don’t want to say the skillset. Still, you don’t have the strength of seeing where your packages exist. What are you selling? You might want to hire an operations person first. And looking at this becomes important. I have been in many meetings where this went the opposite way it was supposed to, and, you know, some, some companies get pretty far along. They don’t even have any internal process or any way to make, you know, the packages that they’re selling. So I think that’s where I stand on that.

Pam Didner: In the beginning stage of a startup, your recommendation or advice is to make sure that CEOs look at themselves and understand what they are good at, their strengths or the areas for improvement. And if they are very good at sales, hire someone else that can complement the area they are not very good at. And if they are very good at the process, then hire a salesperson that can amplify and sell the product.

Kayla Graham: That’s right. Yeah. And I mean, there is another piece of this, which is when does marketing come in?

Pam Didner: I was going to ask you about that. Now let’s assume the CEO hires a salesperson and, um, the product is fantastic. They are growing, um, not rapidly, but steadily. So when do you think startups should look into building the marketing team, and should that be in-sourced or outsourced?

Kayla Graham: That’s a tough question because it kind of all depends on where you are. So, you know, is this your first startup? If it is, you might not have a very good personal brand, yet you might not develop any thought leadership.

Maybe no one knows who you are. So if we even look at the marketing funnel, you’re in awareness, you’re in the awareness phase.

Pam Didner: Top of the funnel. Build brand awareness.

Kayla Graham: That’s right. And you know, I think a lot of people try to fast forward through that process, and you just actually can’t; people have to know who you are. And as you’re building your company, that is a very interesting marketing story because it helps you build authenticity in your brand. Especially when we’re doing B2B, people don’t want to connect with the machine. They still want to connect with a story. Yes, they want a solution that works. Still, ultimately they want to connect with the story behind that and the authenticity. I think there’s a lot of value in as you’re building. Even if you’re not doing traditional marketing, just documenting your story on LinkedIn and building up thought leadership that way.

I think it does a lot, even just, you know, to build the awareness: “here we are.”

Pam Didner: But you know, building brand awareness. I mean, brand awareness is such a big word. You know, a lot of times when people think about brand awareness, they will like, “oh, everybody needs to know who I am.” For startups, their budget is limited, and the paid part of it – it doesn’t matter if it’s paid social or even a paid media effort – paid is kind of expensive. I understand that doing LinkedIn or having the content on your website and regular organic outreach is important. But without a budget is very, very hard to build brand awareness. What is your thought on that?

Kayla Graham: I completely agree. Uh, without a budget, I think everything is hard. That’s why the CEO ends up being the marketer half the time. But I think it’s all about the potential that marketing can bring you? have you sat down and looked at if I make a marketing plan? What will I achieve from that? What is the best-case scenario, What is probable?

Also, what can I achieve from that? And figuring out when you should start to implement that.

I don’t know that it’s necessarily about how much revenue you’re making, and I understand that budgeting is tough. But you do have to put some of it aside for marketing. In the beginning, that means you probably are outsourcing to an agency, which is okay.

I will say this – if you don’t have someone on your side dedicated to reviewing strategy, reviewing the marketing plan, reviewing the content coming in, sitting down and approving it and making sure that it ticks the boxes to hit your ideal customer profile. You’re going to be in trouble.

So that happens a lot that you don’t have anyone on your site directing traffic. And even if you can just get someone part-time to do it, I think it makes a big difference.

Pam Didner: Somebody needs to represent a company, and that person can either be part-time, or they can be full-time, but having a CEO or somebody who wears multiple hats, I don’t think that will work very well.

Kayla Graham: At the end of the day, that usually is what happens, at least at first. In the beginning, the CEO does have to do a lot of hats, but I think there’s also an issue, too, where people don’t realize how much time it takes to review that content to access.

Pam Didner: Talk to me about that! Oh my God. Do you know how many times I have to talk to my clients, as a senior manager, of liking my client, and there was like, “oh, that should be done like tomorrow, tomorrow, right?” “No, that’s not true.” We have to go through the process. And on top of it, even the image you use for LinkedIn has different sizes for Twitter and Facebook. Right? And also need to write a copy a little bit differently for different channels.

I agree it takes quite a bit of time to get that done. And a lot of time managers, senior managers or salespeople don’t understand how time-consuming the marketing is, especially digital marketing, you know, nowadays the modern marketing, how time-consuming these tasks are.

Kayla Graham: It’s so time-consuming. I always make this joke, you know, that people like to wave a magic wand–the marketing magic wand– and everything is just done. Still, unfortunately, it doesn’t work that way. Like we don’t write a blog post, and then suddenly you’re on page one of Google. It just doesn’t work that way. It takes time and

Pam Didner: It’s a long play.

Kayla Graham: Absolutely. Absolutely. And even if the CEO says, “okay, I’m going to review the content.” “Okay, great. You’re reading it, but are you tying it back to your customer profiles to ensure that the message makes sense? Do you think about your audience, of what you know about them? Are you ensuring it’s ticking the boxes of the information you’re trying to give your audience? What is the point of this content that you’re making this blog post?

Pam Didner: I 100% agree.

Kayla Graham: And, you know, it is a major, major time commitment to sit there and do all that. And on top of that, too, “okay, so you found the best ghostwriter in the world. Congratulations. That is already very, very hard to do. So well done. Well, and that’s the thing to make sure that you’re not going to get back something that’s useless. That means you have to do a lot of work on the front end, providing a brief for that writer. If they are the best ghostwriter in the world, you still have to do that. And if you don’t have a dedicated marketing person on your team to even handle doing those briefs, it can become just so cumbersome when you get the piece-

Pam Didner: Yeah, because, because if you don’t do that, prep work in advance, honestly, in a way you are not giving your agency or contractor direction. Right. So they can take any direction they want. And then, of course, when they present information to you and you were like, “What? This is not what I want! But you think I give them a specific direction. You need to provide a direction first.

Kayla Graham: You hit the nail on the head there. And this is what we’re talking about when you get into revision D7, D8, draft number nine, draft number 10. You know, it ends up being just way more of a time suck for everyone. It’s not a good situation for anyone. So yes, you have to provide those directions, and it becomes challenging if you’re the CEO trying to do everything yourself. Having that one dedicated person does, helps.

Pam Didner: Yeah. I 100% agree. So now we have a dedicated person, a marketing person that works with agencies and contractors and creates a plan. So what are the tools that the marketing and sales must have, uh, to make sure that the whole thing is running smoothly?

Kayla Graham: Anything that automates processes that are typically manual and horrible to do number one in my book is an amazing tool. So to give you an example, you always need a project management tool of some kind. Does your project management tool integrate with any of the other tools you’re using? So just for me, from a user perspective, my team does a lot of our talking internally on Slack because we’re a remote team, as many teams are these days. Things come up in those discussions that end up being tasks, and then they just get lost in the sea of nothingness.

Pam Didner: The conversation.

Kayla Graham: Exactly. But what I love about it is that there’s a tool right inside of Slack that can make that a task right in our project management software. Boom. It goes in, and it doesn’t get lost. Now, if we’re talking about marketing and sales, talking to each other, having a good CRM and a good CRM process is super, super important. So to me–I mean, I will die on this hill– I think that HubSpot is the best one, and there’s always more integrations coming with it. Even their SEO tools are starting to knock it out of the park and compete with WordPress well. So, I mean, I’m very pro-HubSpot.

Pam Didner: Really? So the thing about HubSpot, I have several friends that use HubSpot to build a website. The loading speed is way too slow. I’m not necessarily in agreement with that. Sorry.

Kayla Graham: Well, and that’s fair because the other disadvantage too about them is that they only have a few templates; so they’re not yet at the customization level that says WordPress is at, but I do think it’s good to start to come and, you know, we might see that in the next few years. Now, suppose we’re talking just marketing and sales, having visibility into what each other are doing. In that case, I think the HubSpot CRM tool works well for that. There has to be a communication between sales and marketing and, you know, I think this is just like an age-old battle where sales and marketing don’t get along.

Pam Didner: I think it’s not like they don’t get along. Often, it is just a matter of having different goals or approaching things a little bit differently. When I say they have different goals, I think the overall business goals stay the same. Still, once that’s translated down to a different organization, it tends to be different. For example, the marketing maybe they focus on lead gen, or they focus on brand awareness. On the sales side, they tend to focus on the middle of the funnel, the purchase funnel or the bottom of the purchase funnel.

So the focus tends to be different, but they are still trying to achieve the same business objectives. Does that make sense? So it’s just the way they approach things or the things that they will do or want to accomplish at that time. They are not necessarily aligned.

Kayla Graham: Yeah. I’m with you on this and how I like to look at it as like swimming in a pool. We’re all swimming towards the end of the pool, and we all have a lane. We all have a lane that we’re swimming in, right?

Pam Didner: Yeah. I agree with you that the sales and marketing alignment is hard. It’s much harder to see because I work with global enterprises, and many of my clients are big enterprises. And because they are so big and having the challenge to align the sales and marketing tends to be much harder because both sides have a very big organization. The FYI is very hard to align from time to time, or the alignment needs to be driven from the top. But I always get a sense–and by talking to several startups that I’m close to–the sales and marketing tend to be very close. Is that the case? What do you see in reality?

Kayla Graham: Well, yes, but also no (both laugh). As we said, everybody is swimming towards the end of the pool–towards the same goal. So yeah, they want to sell and create revenue. That’s what everybody’s trying to do. I think that marketing, especially in a small company, though, is split up over so many tasks that it becomes hard to support their own internal sales team when a lot of their efforts are focused on external factors. The second part of that, where I see animosity happening, is okay, so sales will act on the leads generated by marketing. They’re going to take the MQLs, right?

Pam Didner: And they will say, “it’s not high quality.”

Kayla Graham: Exactly. It’s not high quality or, you know, “this lead is, not warm enough.” Something is going on in the process internally that things aren’t as far along as they should be before it’s passed off to the sales team. And that often has to do with KPIs and metrics, especially in a startup. You’re trying to carve out your piece of the pie, which is what’s my bonus structure going to look like this year? And how much budget is my team going to get? And to do that, you have to, you know, hit your OKR is hit your KPIs, and that could be X amount of leads. So, you know, someone signs a form to view a white paper, is that a lead? Well…

Pam Didner: No (both laugh).

Kayla Graham: And sometimes those are getting passed on, and they’re not high quality when they come to sales, which creates a problem in the process and a problem for sales. So, you know, I have to be honest, I haven’t seen yet a good example of this working super, super well.

And, and I’m sure that within the time it will. It’d be really interesting to get your perspective on how that works in big companies. Because I imagine the bureaucracy and red tape around making decisions can be super, super hindering.

Pam Didner: Yeah, it is. It’s very hard to align sales and marketing in big organizations. For example, if you’re talking about a global enterprise and the sales side, they focus on multiple different verticals; on top of that, they also have a different account. Right. The accounts usually have different levels. You have this global, national account, the mid-size accounts, and then you have – they call it SMB the small business accounts.

And on top of it, sales tend to be the organization probably structured by industry or regions. So in terms of supporting sales, you have so many variables that the marketing team has to consider. So there are layers and layers of complexity in the big organization in terms of what marketing can do to support sales. And on top of it, you mentioned another thing: the processes.

When I work with the marketing team supporting sales, I always tell them to take baby steps, especially in the bigger organization. There are so many issues that need to be addressed, so what are one or two issues we can address now? You know, and identify some of the low hanging fruits that you can. You can take care of it in a very short time. The long-term collaboration or process, or even the data integration that needs to happen in the backend, usually requires several quarters of planning, sometimes even a year. And you have to look at it from two different perspectives if you will.

Kayla Graham: So I’m glad you brought up the baby steps because I think this is important, even just in startups when sales and marketing are working together. It goes even into content planning and strategy. Startups and still, I think big businesses too–and I know this is a gross word, and we’ve heard enough of it in 2021–but agility is key. And we have learned that. And if we have this big plan with not a lot of flexibility in it, whether it’s the sales side or the marketing side, and things change, well, then you’re in trouble.

So there’s a certain level of agility that needs to be built into that for a quick change. And like you said, it can be so difficult to do that when you’re planning three quarters a year in advance, it’s like, oh my goodness, like, how are we going to change this now? It’s COVID; it’s the Suez canal. This and that.

Pam Didner: In general, I still encourage my clients to create an annual plan and like 2020 to play in 2023. But review your plan every quarter and adjust, like going quarterly planning. So that’s another way, but you have to be pretty disciplined. And that’s just another way to actually kind of be agile. I remember. You know, in 2008, the great recession, right when it hit and literally within the quarter, our marketing budget got cut in half.

Then when it gets cut in half, you have to prioritize. You have to determine, “okay, what are the products that we need to focus on? Also, what are some of the tasks we need to kind of de-prioritize? And why can we do with the limited budget that we have?” So, I do agree with you that re-planning is very, very critical. And I usually suggest my client do it like every single quarter.

Kayla Graham: With how fast startups seem to change direction, I find that there is almost more value in being disciplined to do it every quarter. And if you don’t, if you don’t do it for the year, then guess what? You have to do it every single quarter (laughs).

Pam Didner: Yeah. That was true. That is true. So, um, what are some of the challenges that companies tend to encounter, especially if they are growing very fast or not growing at all? What would be your recommendation in terms of how to address these challenges? If you can name one or two, that would be great.

Kayla Graham: Yeah. So quick growth is always a good problem to have, but it creates a lot of really sticky internal problems. And one of the things you brought up earlier was the MarTech stack, and it creates problems with the MarTech stack because the tool you had earlier might not be any good down the road. Then you get a new marketing manager, a new CMO, and they roll out a new tool. And now you have a tailspin problem as well because you’re paying for a bunch of tools that you’re not even using. Nobody knows what processes to use. Nobody knows what tools to use. It’s fragmented. All of your information is siloed and living in different places, and that’s pretty much a nightmare and a common one.

And you know, when I think about common problems, that is like one of the biggest ones. On the other side, if you’re not growing. I mean, uh, I think the problem’s pretty obvious. I mean, you’re losing talented team members because they can feel the death in the air, and they’re looking for other jobs.

Pam Didner: Yeah. I hear you. I just feel that we are in a great time, probably the best of the time in terms of technology. Still, worst of time in terms of competition, especially if you’ll feel any SaaS-based platform because the entry to build those platforms, the cost is pretty low. And everybody can build something very quickly. And, if your product just happened to hit the core at the right place at the right time, it can take off. But that doesn’t mean that you know you will enjoy that longevity of possibility. No, a lot of time a year or two later, there’s another, uh, players that come into play and can do so much better than you. And all of a sudden, in two years or three years, your product is just obsolete.

Kayla Graham: Yeah, I agree. You know, are really good examples of that, I think–and sorry if I’m calling anyone out here, but when I looked at what happened with the pandemic, when all these teams started working at home and Zoom became popular a few years ago before Zoom, I didn’t even know what it was. We always used Go to Meeting at my offices, and I seem to like disappear and go extinct. I think that’s a perfect example of someone competitive. I was ready for it when everyone was working at home, trying to keep that momentum up when you’re hot. That’s a really hard job.

Pam Didner: I 100% agree with you. It’s a daily grind.

Kayla Graham: It is. I think that plays into this dialogue that we’ve been given about the hustle culture. How this is kind of like glamorized now, even to do this. How hard can you work?

Pam Didner: Exactly. So I like to summarize many insights that you share with us. Number one is very much that it depends on the CEO’s strengths and weaknesses for your startup’s first hire. And if you know what you are good at, hire somebody to compliment you. It is nice to hire one person dedicated specifically to the marketing function. That person can put the plan together and be a conduit between the agency and the CEO or the senior management. This person can also review many content or copies or anything created by agencies and contractors. The third thing you mentioned is finding tools that will automate your processes. Still, at the same time, the tool needs to be integrated into the existing tools that you use.

Kayla Graham: A hundred per cent.

Pam Didner: And in terms of a sales and marketing alignment, I guess, you know, you and I talk about how challenging that needs to be, I think that needs to be kind of top-down driven–if the, or the VP of marketing and VP of sales are very closely aligned, that kind of message will kind of permeate down to the worker bee level. But if they are doing their things separately, then the teams will just be siloed. So I think that needs to be top-down driven.

Kayla Graham: Exactly. 100%.

Pam Didner: Okay. Thank you so much, Kayla, for joining me, and so happy to have you on my show. This was a lot of fun.

Kayla Graham: Thank you so much for having me.

What can Pam Didner do for you?

Being in the corporate world for 20+ years and having held various positions from accounting and supply chain management, and marketing to sales enablement, she knows how corporations work. She can make you and your team a rock star by identifying areas to shine and do better. She does that through private coaching, keynote speaking, workshop training, and hands-on consulting. Contact her or find her on LinkedIn and Twitter. A quick note: Check out her new 90-Day Revenue Reboot, if you are struggling with marketing.