What does it really take to excel as a B2B marketing leader?

We asked veterans to share their best advice at Drive (our in person event) last fall.

Because the most valuable advice comes straight from people who have actually done the job.

Tara Robertson, CMO at Bitly and previously at companies like Sprout Social and Hotjar, joined Amrita Mathur, previously a marketing leader at Zapier and ClickUp, and Peter Mahoney, former CEO and founder with extensive marketing leadership experience.

And they offered a masterclass in modern marketing leadership that went way beyond the usual playbook, including:

• Why business fundamentals matter more than marketing tactics
• How to maintain strategic focus 
• Ways to build authentic leadership presence
• Strategies for balancing short-term results with long-term vision
• How to get unstuck when you’re burnt out

So whether you’re a VP of Marketing or CMO today or you’re eyeing a leadership position down the line, this article is packed with tactical advice to help you become the best of the best.

Foundations of Effective Marketing Leadership

Before diving straight into tactics and strategies, successful marketing leaders build their foundation on two critical pillars: deep business understanding and well-honed intuition. 

And while these may seem obvious, they're often overlooked in favor of more visible marketing activities (like changing the website).

Know the Business Inside and Out

Becoming an exceptional marketing leader starts with understanding the fundamentals of your business. For Peter, this starts with building a strong relationship with the finance leader ASAP. 

Because when you deeply understand how your company makes money, you build trust and getting buy-in across the company becomes much easier.

This means:

• Having regular conversations with finance about business drivers and revenue goals
• Understanding the company's financial model and multi-year plan
• Learning how different aspects of marketing impact the bottom line
• Speaking the language of business impact, not just marketing metrics

This business-first mindset establishes your credibility from the get go and shows you’re committed to marketing that supports company objectives.

Trust Your Instincts

While data and analytics play a crucial role in marketing decisions, seasoned marketing leaders know when to trust their gut. Looking back at his early career, Peter shared, "I wish I trusted my instincts more earlier." 

Because if something seems off, it probably is. Developing this intuition comes from:

• Building experience across different scenarios
• Learning from successes and failures
• Constantly testing assumptions against results
• Balancing data-driven decisions with experience and judgment

This instinctual knowledge becomes particularly valuable when navigating uncharted territory or evaluating new opportunities where historical data may not exist.

Setting the Right Goals and Strategy

Once you understand the business fundamentals, the next step is to establish clear goals and overall strategy. This isn't just about setting arbitrary targets or creating complex frameworks. It's about developing a roadmap that aligns everyone in the organization. 

The Importance of Clear, Aligned Goals

Effective goal setting gives the entire team direction and focus. It’s the backbone for marketing success.

The best marketing leaders:

• Set clear business-aligned objectives that cascade down to team-level goals
• Break annual goals into quarterly milestones with monthly and weekly check-ins
• Include learning goals alongside performance metrics when testing new approaches
• Establish clear ownership for each goal with specific accountabilities

Rather than getting caught up in complex goal frameworks, successful leaders focus on simplicity and clarity. As the panelists noted, if your goals can fit on a napkin and everyone understands them, you're on the right track.

Strategy: How You Get There

Strategy is the bridge between where you are today and the targets you want to hit. Peter explains, "Your goal is getting to the top of a hill. What's your strategy? Maybe I can climb up the front, the steep part, or maybe I go the long path around the back."

This clarity on the "how" helps the rest of the team figure out the right tactics and tools for the job. Effective marketing strategies:

• Provide a clear path to achieving defined goals
• Consider available resources and constraints
• Remain flexible enough for adjustments
• Maintain consistency in direction despite short-term fluctuations

The panelists emphasized that strategy doesn't have to be complex. It should be clear enough that every team across the org understands it. 

Balancing Short-Term and Long-Term

One of the most challenging aspects of marketing leadership is balancing immediate needs with future growth. Tara recommends looking at your natural growth curve first: "What's the gap to where the business needs to be? What does our natural growth look like if we do nothing else?"

Successful marketing leaders:

• Paint a picture of the future state to guide current decisions
• Allocate resources strategically between immediate needs and future growth
• Consider both natural growth trends and aspirational targets
• Build for the future while delivering current results

This balanced approach helps marketing leaders avoid the trap of sacrificing long-term growth for short-term gains or investing too heavily in future initiatives at the expense of current performance.

Developing as a Marketing Leader

You don’t need to master every channel or execute perfectly to be an amazing leader. But you do need to be committed to continuous growth and have a deep understanding of your strengths and weaknesses. 

Optimize for Learning

At a time when Amrita was losing sleep over hitting her targets, her CEO gave her a piece of advice that has stuck with her: "Optimize for your velocity of learning." This perspective gave her peace of mind and the freedom to focus on being a sponge.

To accelerate your learning:

• Run rapid experiments with clear learning objectives
• Create feedback loops that speed up decision-making
• Give yourself and your team permission to try new approaches
• Focus on extracting insights rather than perfect outcomes

This learning-focused mindset is particularly valuable in new roles, rapidly changing environments, or when testing unproven strategies.

Recognize You Don't Need to Be an Expert in Everything

Rather than trying to master every marketing discipline, successful leaders recognize their strengths and build teams and networks to complement their abilities. They:

• Know their areas of expertise and where they need support
• Build diverse teams with complementary skills
• Develop networks of experts they can turn to for guidance
• Focus on empowering specialists rather than trying to do everything

This approach not only improves marketing outcomes but also reduces the pressure and stress that comes from feeling like you need to know everything about everything.

Know Your Superpower and Kryptonite

Peter has found that, "Your superpower is related to your kryptonite." This recognition that strengths and weaknesses are often two sides of the same coin helps leaders embrace their natural style while mitigating potential blind spots.

For example, Peter describes himself as "calm and unflappable" (his superpower), but acknowledges this can make him "unreadable" to team members (his kryptonite). 

Understanding this can help leaders:

• Leverage their natural strengths 
• Create systems to address potential blind spots
• Communicate their work style to help team members adapt
• Build teams that complement their leadership approach

This self-awareness allows marketing leaders to be authentic while leaving plenty of space for development and growth.

Taking Calculated Risks

Growth often requires stepping outside your comfort zone. When asked about career risks that paid off, Tara shared how networking has helped her career in a major way: "The biggest risk I ever took was walking up to that first person...and saying, hey, buddy, will you mentor me?"

For Peter, it looked like, "walking away from a big job, making a ton of money, and going to start a company where I made no money for three years." 

To get really good at taking calculated risks, you have to:

• Identify opportunities that align with your goals and values
• Assess potential risks and rewards realistically
• Build networks that support your growth and development
• Look at challenges as opportunities for growth

The key is to make these leaps intentional rather than impulsive. So when you look back you’re not kicking yourself, you’re proud.

Working Effectively Across the Organization

Success depends heavily on relationships. The most brilliant strategy will fail without buy-in from key stakeholders, which is why effective marketing leaders prioritize building strong connections throughout the organization—especially with those who may not naturally align with marketing's perspective.

Master Communication at All Levels

"If you don't want to communicate, don't become a marketing leader," Tara emphasizes. Communication isn't just an occasional skill for marketing leaders – it's the foundation of their effectiveness.

Successful marketing leaders:

• Create proactive update rhythms with their CEO and key stakeholders
• Explain marketing strategies and results in business terms
• Establish clear communication channels in all directions (up, down, and across)
• Adapt their communication style to different audiences and situations

This communication mastery helps marketing leaders build the credibility and trust needed to drive initiatives forward.

Build Productive Relationships (Even with Difficult Personalities)

Each expert acknowledged that not every work relationship is easy. When asked about working with challenging counterparts, Amrita shared, "Almost always. Like, I literally can't remember a time where that hasn't been the case."

Rather than letting difficult relationships derail progress, effective leaders:

• Focus on shared business goals despite personal differences
• Address challenges directly and professionally
• Resist the urge to use the CEO as a referee
• Find common ground to build working relationships

As Tara noted, “If you don't like each other, who cares? You're running the same business, you've got the same goals. Figure it out. And I think the important thing is, a lot of people say, “Oh, sales, product, they have to be your best friends.” Best friend doesn't mean that you're sitting down and you're kumbaya ing and have the best time together. It means you debate and that you've got challenges and that you're having those shared goals.”

Understand Your CEO's Perspective on Marketing

Marketing leaders must navigate their relationship with the CEO carefully. While the "CEO is not the CMO," as Tara points out, they often have strong opinions about marketing. Successful marketing leaders:

• Establish regular communication rhythms with their CEO
• Proactively provide updates on marketing initiatives and results
• Frame marketing discussions in business impact terms
• Recognize that CEO interest in marketing is generally positive

Tara recommends, "If I don't hear from him in a week, I send him an update. Here's all the things we're working on. Here's how we're trending with the numbers. This is what the forecast is."

Leading Through Challenges

Even the most skilled marketing leaders face periods of uncertainty, pressure, and burnout. What separates exceptional leaders from the rest is how they navigate through the storms. 

Stick to Your Strategy During Short-Term Fluctuations

When results dip, the pressure to make dramatic changes intensifies. However, Tara cautions against knee-jerk reactions: "Don't get stuck in the short-term gains if your numbers start to go in an opposite direction. Stick with the things that you believe in."

Effective marketing leaders:

• Distinguish between normal fluctuations and concerning trends
• Watch for patterns over time rather than reacting to daily changes
• Make tactical adjustments while maintaining strategic direction
• Communicate confidence in the strategy during temporary setbacks

So the next time the results are falling short, resist the urge to jump too quickly and double down on the strategies you have confidence in. 

Find Sources of Energy and Inspiration

Leadership can be draining. Especially during challenging periods. No one can be inspired and pumped about their job 100% of the time. 

So whenever they’re in a rut, resilient marketing leaders:

• Develop a network of trusted mentors for support and perspective
• Identify activities outside of work that recharge them
• Recognize their personal limits and recovery needs
• Build in time for reflection and renewal

Tara’s playbook here is simple: "I know I have a two-month expiration, so every two months I need a day where I just go get my energy and then bring it back to refuel the batteries."

Be Vulnerable with Your Team

Rather than projecting an image of perfect confidence at all times, the most effective leaders share appropriate vulnerability with their teams. Tara explains, "I have vulnerable moments every day. Like, I will tell my team when I'm stressed. I try to lead by example so that they can hopefully do the same."

This authentic approach:

• Creates a safe environment for the team
• Models healthy workplace behavior
• Acknowledges the challenges of growth and change
• Builds stronger team connections and trust

There’s a fine line between oversharing and not sharing enough with your team. So you have to find what feels right for you. But vulnerability is not a weakness. It’s a way for you to build meaningful relationships with your team.

Your Path to Becoming A Top Marketing Leader

Becoming an incredible Head of Marketing means embracing both the art and science of business leadership.

The most valuable takeaway? Excellence doesn't come from perfecting every marketing discipline. It comes from understanding your business deeply, communicating in all directions, making strategic decisions with confidence, and finding your authentic leadership voice.

The leaders who stand out don't just execute flawlessly—they think differently. They see beyond campaigns to business impact. They build relationships across organizational boundaries. They maintain strategic vision while navigating daily challenges.

The difference between good and exceptional often comes down to consistent, intentional improvement in these fundamental areas.

So what are you going to focus on getting a little better at every single day to become the absolute best leader you can be?