Why GTM Rebuilds Start With Clarity, Not Campaigns, with Corey Livingston

A company reaches a key moment. The strategy changes, the target buyer shifts, and leadership decides to focus on the enterprise market.

But the go-to-market system underneath the business may still be built for an earlier stage of growth.

Corey Livingston shares why rebuilding your GTM should start with understanding and clarity, how marketing can build trust with sales before results appear, and what leaders should measure before the pipeline is visible.

About this episode

Financial reports show how a business is doing, but they don’t show if the go-to-market engine is ready to support the company’s next phase of growth.

That is the tension at the center of this conversation with Corey Livingston, Vice President of Marketing at DartPoints.

Corey has spent more than two decades leading B2B marketing through growth and change. She has worked inside companies moving upmarket, entering new segments, and trying to build several GTM motions at once.

Her starting point is not another campaign.

It is understanding the growth hypothesis, determining whether each motion is in the build, activate, or scale phase, and getting the organization aligned around what it can realistically produce next.

We talk about why moving into enterprise requires more than changing the target account list, how marketing earns credibility with sales, why alignment must extend below the CRO, and what leaders often get wrong during the first 90 days of a GTM rebuild.

About Corey Livingston

Corey Livingston is the Vice President of Marketing at DartPoints.

She has more than two decades of B2B marketing experience, including leadership roles at Level 3 Communications and OneNeck Solutions, as well as fractional CMO work across multiple companies.

Her work focuses on GTM strategy, sales and marketing alignment, enterprise growth, and helping companies build the operating systems required for their next stage of growth.

Connect with Corey

Follow Corey Livingston on LinkedIn

Chapters

00:00 Why healthy dashboards can hide a broken GTM system
00:49 What dashboards miss in a GTM rebuild
02:36 Why moving upmarket changes the entire motion
05:35 How to diagnose the gap between strategy and execution
09:02 How marketing earns sales’ trust before results
17:58 How to decide which GTM motion comes first
21:00 What to measure before pipeline shows up
26:23 What leaders get wrong in the first 90 days

A few things worth taking away

Financial reports show business performance. They do not show whether the GTM system is mature enough to support the next stage of growth.

GTM is a lifecycle, not a switch. Leaders need to know whether a motion is being built, activated, or scaled before deciding what to measure.

Moving upmarket is not just a strategy shift. Enterprise buyers require more credibility, stronger proof, deeper content, and tighter coordination with sales.

A corporate strategy is not the same as a go-to-market strategy. The organization still needs clarity about how growth will actually happen.

Sales trust comes from clarity, follow-through, and quick wins, especially while the longer-term GTM system is still being built.

Alignment with the CRO is not enough. Marketing also needs to earn the trust of frontline sales leaders and the people doing the work every day.

You cannot scale every motion at once. Investment decisions should connect to the company’s growth hypothesis, resources, timing, and near-term revenue needs.

Pipeline is a lagging indicator. Operational readiness, engagement from the right accounts, and qualified meetings can show whether the motion is beginning to work.

For an early enterprise motion, one of the most useful questions is: are we meeting with the right person at the right account, and are they moving to a next step?

The first 90 days of a GTM rebuild should begin with diagnosis. Leaders often create problems by trying to fix the system before they understand it.

A few lines that stuck with me

“I look at GTM as more of a lifecycle, not a switch.”

“A corporate strategy and vision is not a go-to-market strategy.”

“Sales trust comes from creating clarity. It comes from follow-through and quick wins.”

“You can’t scale everything at once.”

“You can’t get to pipeline without engagement.”

“Are we getting a meeting with the right person at the right account?”

“Most leaders try to fix things too fast in the first 90 days.”

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Transcript

Brian Carroll: Welcome to The B2B Roundtable. I’m Brian Carroll, and we’re going to talk about something people don’t often talk about.

A company hits an inflection point. The strategy shifts, the buyer changes, and the dashboard shows green. But the system underneath was built for a different version of the business.

The gap doesn’t show up in a report. It shows up when things start to stall, and nobody can explain why.

My guest today is Corey Livingston. She has spent more than two decades in B2B marketing, leading at companies including Level 3 Communications and OneNeck Solutions. She has also done fractional CMO work across multiple companies.

Today, she is serving as the Vice President of Marketing at DartPoints. I invited Corey because she has been through these inflection points in several different seats.

Corey, welcome.

Corey Livingston: Thank you, Brian. It’s great to be here. Thanks for having me on.

Brian Carroll: We’ll dive right in. When you step into a GTM rebuild, perhaps at a mid-market company, what are the things you usually see first that dashboards don’t show you?

Corey Livingston: When you step into a company that is evolving its strategy, in my experience, in almost all cases, that evolving strategy involves moving more upmarket.

You look at the numbers. You look at the financial reports. You talk to all the right people. It tells you what is happening in the business, how it is performing, and its underlying health indicators.

But it doesn’t tell you whether the go-to-market engine is mature enough to support the next stage of growth, the next inflection point, or the new segment you want to penetrate.

You have to start by diagnosing where you are. Where is the business in the go-to-market lifecycle? Are you in the build phase, the activate phase, or the scale phase?

I look at GTM as more of a lifecycle, not a switch.

You don’t just declare that you’re moving upmarket or moving into a PLG motion, or whatever it might be, and then it happens. You have to understand where you are.

If you don’t know where you are in the lifecycle, you’ll end up measuring the wrong things, investing in the wrong places, and expecting outcomes the operating system isn’t ready to produce yet.

Brian Carroll: That makes a lot of sense. Could you give an example, without naming the company, of where that stood out to you and what you did?

Corey Livingston: As I mentioned, I’ve worked across many different companies that were operating in either SMB or mid-market. That was their customer profile, and many of them wanted to move into enterprise.

The deals are larger. The revenue is stickier. There is more opportunity to differentiate.

I used to have a boss who would say, “Where there’s mystery, there’s margin.” There is also more opportunity to be consultative.

Brian Carroll: Mm-hmm.

Corey Livingston: But going into enterprise or moving upmarket, whether it is the lower end of emerging enterprise or the Fortune 500, is not just a strategy shift. It is a motion shift.

The go-to-market operating system for enterprise is fundamentally different from SMB or mid-market.

I’ve worked in environments where companies were pursuing all three segments: SMB, mid-market, and enterprise.

In SMB, buyers move fast. There are fewer people involved in making the decision. The stakes are lower, and the go-to-market engine can rely on lighter content, simpler messaging, and more transactional motions.

You also tend to get much more inbound from SMB than you would from enterprise.

Enterprise is the opposite. The cost of entry and the burden of proof are much higher, not just in what you need to spend, but also in the credibility you need to get the door open.

Enterprise buyers operate in much more complex environments. In my case, I’ve always worked in the IT and technology sector, where IT environments are highly complex.

The stakes are much higher for the people influencing or making the decision if something goes wrong. There is much more risk involved.

They want credibility and familiarity. It is the old saying, “Nobody ever got fired for hiring IBM.” There is still a version of that in our modern marketing world, especially when you move upmarket.

That means your GTM system has to evolve. What worked for SMB and mid-market is not necessarily going to work. It may provide some foundational elements, but the system still has to change.

You need deeper content. You need much clearer use cases. You need reference customers who have worked in these enterprises before. You need strong stories, proof points, more orchestrated outbound, and much tighter alignment with sales.

You’re going to be working hand in glove with sales. You also need a sequencing model that matches how enterprise organizations actually buy, which is a more complicated buying journey.

Brian Carroll: How do you tell when a strategy has changed, or needs to change, but the GTM system hasn’t caught up yet?

Corey Livingston: In my current role and my previous role, I had a significant part in helping shape the GTM strategy.

The first thing I do is understand the growth hypothesis.

When I walk into a business, the first question I ask is: What is the hypothesis for how we are going to grow? What channels are we using right now? Are those the right channels?

I interview the executives, the C-level team, and everyone on the go-to-market team.

The go-to-market team is not just marketing. It includes product, sales, and, in my industry, solution architecture.

It is about doing the research, conducting interviews, and asking the right questions.

Where do people think the go-to-market system is today? How well is it working? Where is it not working?

I’m looking for areas of agreement and areas of difference. I want to make sure those differences are not so significant that they could undermine the strategy we need to build for the next phase of growth.

I start by asking what we have today and whether that operating system can get us to the next phase of growth.

I can’t necessarily determine that on my own. When you’re building GTM, one of my strengths is bringing everybody together, getting everybody on the same page, and listening deeply.

Those are considered soft skills, and I don’t think they get enough attention. But that is the first place I start.

I don’t walk in and immediately start executing a GTM plan.

In many environments I’ve entered, there isn’t really a GTM strategy. There is a corporate strategy. But a corporate strategy and vision are not a go-to-market strategy.

A corporate strategy does not explain how you are going to activate in the market and begin producing results.

You also can’t scale everything at once.

I have to prioritize the areas where we have leverage and anchor everything to the growth hypothesis.

What are the sales quotas? What are the revenue projections? What motions already exist, and where are they in the lifecycle?

If the growth hypothesis says growth will come from retention and expansion, I would start there, unless there is foundational work required that would delay our ability to activate and reach our sales or revenue numbers in a way that conflicts with the plans presented to the board.

Then I look at the next motion. It could be channel, inbound, or events.

Which motion is most mature? Which one can we activate fastest? Which one aligns with the near-term revenue picture?

That is where I start.

Brian Carroll: Those are some great pointers for people thinking about moving upmarket or entering the enterprise.

You mentioned sales quotas and getting alignment with sales because this is a significant shift for the organization.

Corey Livingston: Yes.

Brian Carroll: How do you build trust with sales before you have results to point to?

Corey Livingston: That is always much more art than science.

In my experience, sales trust comes from creating clarity. It comes from follow-through and quick wins.

It is hard to earn sales trust, but it is very easy to lose.

I don’t necessarily come in with a 90-day plan for sales. I would probably do that for my CEO, but not necessarily for the sales organization.

They need clarity. They need enablement. They need early wins.

My strategy is always to build trust by helping them move faster, not by asking them to wait for the perfect GTM system to materialize before I deliver anything.

Early in my career, and I think this is true for many of us when we’re starting out, we think we know it all. We’re going to do the things we know need to be done, and sales can wait because they are not part of the strategy.

Now, when I walk into a new role, I’m working with the executive team and the GTM team to understand where we are, where we need to go, which motions will get us there, what we already have, what we need to build, and what we need to activate.

At the same time, I’m thinking about how we can get into market faster while we are building the operating structure we need.

I think sales appreciates that.

It starts with talking to them and listening. What do you think you need to be successful?

It is basic, but it also requires honesty.

Here is where I am. Here is how long I think it will take based on the budget and resources I have.

During those first 90 days, I will probably work twice as many hours just to put something in front of them so they can begin seeing traction earlier.

They appreciate that you are doing what you can to enable them and that you are not making perfect the enemy of good while you build the longer-term plan.

Brian Carroll: Could you share a lesson or a story about something you wish you had done differently, so someone else might avoid the same mistake?

Corey Livingston: If you’ve been in B2B marketing long enough, you probably have plenty of scratches and bruises from trying to align with sales.

The bigger the company, the harder it is.

I’ve worked at $10 billion companies, $200 million companies, $50 million companies, and $10 million companies. The smaller the company, the easier it is to align.

That is one reason I now like working in a certain size of company, where you can have more impact and where sales and marketing need each other, particularly during an active growth phase.

In larger, more complex companies, I’ve found it much harder to align. The business is more mature at $10 billion, so I’ll add that as context.

The other thing I’ve learned is that sales leaders at the top of the organization are not the only people who matter.

The mid-level sales leaders, the people the teams report to, typically the GMs and sales vice presidents, are often the people individual sales reps listen to first.

Brian Carroll: Mm-hmm.

Corey Livingston: I’ve had experiences where I had total alignment with the SVP of Sales or the CRO, but I was out of alignment with the next layer down.

In some cases, I’ve also worked in environments where sales simply did not want to align with marketing.

That is a broader issue in our industry. Marketing is sometimes not trusted or is seen as lacking industry knowledge. Marketers may be viewed as too focused on pretty colors and pictures and not focused enough on understanding the day-to-day work of the sales team.

In those environments, it is nearly impossible to be successful. Sometimes, you simply have to move on.

Brian Carroll: Mm-hmm.

Corey Livingston: In other environments, it is about continually building trust with the mid-level sales manager.

It is not just about focusing on the highest level of leadership. It is about working with the people in the trenches every day.

What are your objectives? What are you trying to achieve?

You also need to let them know you understand how sales works and ask questions that are not coming only from a marketing lens.

I have never carried a quota, unless you count marketing and selling fractional services, but I know enough because I have embedded myself in those organizations.

When I ask questions from the sales team’s perspective, such as, “Who is your highest-performing rep? Who is your lowest-performing rep? Where do you need the most help?” it helps me align much more effectively.

Then, again, it comes down to following through.

Brian Carroll: The big takeaway I’m hearing is that you cannot just align at the executive level. You have to move one, two, or three levels down to the frontline managers.

Corey Livingston: Yes.

Brian Carroll: Those are the people who see the day-to-day experience of the reps.

Corey Livingston: Yes. Not everyone is able to do this, and that is another reason I now align more with midsized companies.

I talk to reps one-on-one. What are they struggling with? Where do they think they need help?

Even in my current role, if one of my salespeople contacts me and needs help, I will drop what I’m doing to help them.

It is about understanding their world and understanding how they get paid.

As long as the request is aligned with the direction we have all agreed to pursue, those little touches matter.

Maybe you were willing to work an extra hour to help someone pull a list. I don’t care about my title. I will do whatever it takes. We’re all in this together.

That is what people on the sales team and the product team need to feel.

They need to feel that you are just as invested in their success as you are in your own.

Not everyone operates that way, but when someone sees that you are willing to jump in, even if it is just helping write an email or pull a list, it matters.

No matter your level in the organization, those small things go a long way toward building trust and creating alignment.

I will never stop doing them.

Brian Carroll: What I’m hearing is that you’re doing things that help reps have more effective selling time and add value to their day.

At the same time, you’re working on the strategic initiatives that will contribute over the long term while still meeting short-term needs.

Corey Livingston: Yes. It is similar to Maslow’s hierarchy of needs. People need oxygen. They need water.

I’m definitely securing my own oxygen mask, but I also have one to give the sales reps.

Even if I had something due and helping a salesperson was going to put me behind on a deliverable to the executive team, I would have no problem saying, “I need an extra hour or two, or an extra day. I need to help this salesperson. They have a deal on the line, or they need to increase their prospecting activity.”

I don’t think anyone would argue with that. No one ever has.

Marketers have to come down from the ivory tower and understand that, in B2B in particular, most organizations are going to be sales-led.

You have to accept that reality and not fight the system.

I’ve seen many B2B marketers try to fight it. They say marketing should be this or marketing should do that.

But at the end of the day, sales is the tip of the spear.

As long as we are aligned with the go-to-market strategy, marketing has to be the foot soldiers. We provide air cover, but we also need to be on the ground doing reconnaissance and whatever else sales needs to be successful.

That should happen not just at the organizational or academic level, but also one-on-one.

That is the attitude I encourage and look for when hiring people for my team.

Brian Carroll: How do you manage when several different motions are competing for attention? How do you decide what comes first and what has to wait?

Corey Livingston: Once you have the motions built, I’ll go back to something I said earlier: you can’t scale everything at once.

You have to return to the growth hypothesis and understand where you are in the lifecycle.

If you are in the build phase, it may take twice as much time, or even three times as much time, to reach the activation and scale phases.

This is not just a decision I make on my own. It is a decision made as part of the GTM team.

I may be facilitating or leading the conversation, but we all have to agree on where to place our bets in the short term versus the long term while we are building.

We also have to align the investment with those motions.

For example, when you don’t have an established brand in the enterprise, it will take time for buyers to understand who you are and for you to build credibility.

In that case, you might prioritize channel partners.

Large channel partners already have relationships. They serve as technology advisors to CIOs, CTOs, and other leaders in enterprise organizations.

The best short-term path may be to invest in building your partner ecosystem.

Make sure partners are aware of you and your capabilities. Attend their events. They are often the people who will recommend you.

It is rare for a CIO to come directly to a vendor’s website. They may conduct some research, but they are unlikely to fill out a form. That is not how their buying process typically works.

They also have many people prospecting them at any given time.

So you have to ask whether channel is the fastest path to revenue and what the tradeoffs are.

You may have to pay an agent commission in addition to the sales commission, so you have to balance that.

Could inbound be the priority? Inbound is not usually a strong enterprise motion, but you may need to keep investing in it to generate smaller deals while you build toward larger ones.

It really comes down to triangulating where growth will come from.

It could be retention and expansion. If that is the expected path to revenue, you need to assess everything around where you are in the lifecycle, what investment is required, what the timeline looks like, and how much budget is available.

It is like solving a Rubik’s Cube.

Once you decide, you have to get everybody on the same page and make sure the executive team is aligned.

That is what will be communicated to the board. They need to see consistency in the thinking and commitment to the plan.

Brian Carroll: As you measure the plan and its outcomes, I think many marketers treat pipeline as the main scoreboard.

But pipeline is really a lagging signal. It shows what has already happened.

Corey Livingston: Yes.

Brian Carroll: What do you trust as a leading indicator besides pipeline?

Corey Livingston: I trust engagement signals.

Whenever we are launching a motion, we are looking for good signals. We want to understand what is working before we double down on the investment.

I would not say I am risk-averse, but I am cautious.

During almost all of the 20 years I’ve worked in B2B marketing, budgets and resources have been constrained. That is simply the nature of the work.

When we are first investing in programs, I look at different indicators depending on the phase.

If we are in the build phase, the indicators are more about operational readiness.

What did we deliver?

If we are moving into a specific vertical, do we have case studies and references? Do we have thought leadership content? Do we have a dedicated web page? Do we have relevant experience?

Those indicators are more about completing the work we need within a specific period of time.

If we are in the activation phase, we now have enough assets and a minimum viable approach to launch into a specific segment.

You cannot get to pipeline without engagement.

If no one is engaging with you, looking at anything, responding on LinkedIn, responding to email, picking up the phone, or visiting your website, that is a sign that you may need to reassess the strategy.

You are not going to get to pipeline without engagement.

With account-based marketing, which is one of our motions, we look for movement among high-fit accounts.

We look at website intent. Are those accounts visiting the website? What are they doing? What does their search pattern tell us? Does it indicate active research?

We also look at partner-sourced engagement.

Are we getting meetings when we attend partner events? Are partners contacting us about opportunities? What is the quality of our inbound interest? Are people engaging with our content?

It is a great time to be a B2B marketer because you can measure almost everything and have so much visibility.

The challenge is separating noise from a meaningful signal.

Those are the things I look at, and they can be difficult to communicate when you are not yet in the scale phase.

When the motions have not been in market for long, you are trying to communicate progress before the final outcomes appear.

Most organizations, especially the C-suite, are highly outcome-oriented.

They want to know: How many opportunities are there? What is the value? What stage are they in? What is the commit? What is the best case? When will this close?

When you bring them engagement metrics, the reaction may be, “Okay, but what does that mean?”

You have to continually explain why those indicators matter.

Even when you are looking at lagging indicators like pipeline, you still need to work backward.

What are we doing? Are we focusing on the right accounts? Are we prospecting? Where are the leads coming from?

All of those things matter before you get to pipeline.

Brian Carroll: From your experience, are there any key indicators that tell you the company is moving in the right direction and making progress?

Corey Livingston: One of the things we look for is whether we are getting meetings.

Meetings are a major indicator.

To me, that could represent a potentially qualified lead. Is it a qualified meeting? Was there an outcome that led to a possible next step?

That is one of the most important indicators I look at.

There are other signals, such as opens, click-throughs, and whether the right accounts are visiting the website. Do they meet our ICP?

But meetings are one of the biggest indicators.

As you move into enterprise, I think you have to throw BANT out the window: budget, authority, need, and timeframe.

That is especially true when you are just beginning to enter enterprise accounts.

When the motion is early, the question I work on with sales is: Are we getting a meeting with the right person at the right account?

That is what we look at most.

Are we moving to the next step, and why or why not?

That tells us whether it was truly the right person or whether there may have been a product-fit issue.

It could have been a strong, qualified lead. It could have been the right person at the right account and matched our ICP, but perhaps something was missing in what we could offer, and the opportunity could not move to the next step.

That is still an important signal.

Brian Carroll: For someone in the trenches right now, what do you think most leaders get wrong during the first 90 days of a GTM rebuild?

Corey Livingston: I would say most leaders try to fix things too quickly during the first 90 days.

The first 90 days are really about diagnosis.

It may not take the full 90 days. It may take 30. But leaders often either take too long or jump in and try to fix things too fast.

The diagnostic piece is critical.

Listen. Interview every executive. Understand the situation from their point of view.

Many people struggle to answer a question I ask: What does marketing success look like at the end of 90 days or at the end of six months?

That is a very difficult question for many people to answer.

I don’t think that is a bad thing. It means you have an opportunity to shape how you should be evaluated and to educate the organization.

In many companies, when I do receive an answer, it is usually: How many leads did you produce?

But we all know marketing is much more than leads.

You are not going to generate leads if you do not have brand awareness and credibility.

I’m glad brand awareness and credibility are coming back into focus because they are incredibly important.

My advice is to spend time listening, interview the right people, and understand how they think about growth.

Try to surface any conflicting information that could undermine your approach.

If you find conflicting views, bring the people together in a forum rather than addressing it only one-on-one.

You can say, “Here are some things I heard that I’m struggling with. Can we have a conversation about what this means and how we can get on the same page? If we don’t, here will be the impact.”

I think that demonstrates thoughtfulness.

Once you do that, you can also tell the leadership team, “The sooner we align on this, the faster we can move.”

There may also be low-risk activities you can begin while conducting the diagnosis.

For example, in a recent company, we started doing LinkedIn outbound and testing our messaging.

We looked at who was responding. It was low-risk and did not require a large amount of messaging.

Those activities can contribute to what you are learning while you conduct the broader diagnostic work.

Once you have that picture, it becomes much easier for marketing executives to perform effectively.

They have spent time understanding everyone’s point of view, focusing on the areas of alignment, surfacing the areas where alignment is missing, and developing a solution.

That is when you are seen as a more strategic player at the table, but also as someone who can execute.

Brian Carroll: The overarching theme I’m sitting with is clarity and helping the collective team gain clarity together.

Corey Livingston: Most seasoned marketing or GTM leaders know that, but it is becoming a lost art.

I can’t tell you how many times I’ve stepped into environments where people were not talking to one another. They were talking around one another.

It is a skill, and a valuable one, to be the facilitator and the person who brings everyone together.

Brian Carroll: Corey, thank you. I appreciate you joining us today.

For our listeners, here is a question I would like you to take back to your own team:

Are you measuring what you built, or are you measuring whether it can get you where you are going?

Corey Livingston is the Vice President of Marketing at DartPoints. You can find her on LinkedIn.

Thanks again for listening, and thank you, Corey, for joining us today.

Corey Livingston: Thank you, Brian.

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