Planning vs. agility trade-offs

What’s up everyone, today we have the pleasure of sitting down with Anna Leary, Director of Marketing Operations at Alma.

• (00:00) - Intro
• (01:15) - In This Episode
• (04:38) - How to Prevent Burnout
• (05:46) - What Companies Can Do Better
• (07:50) - Agility of Planning
• (08:53) - Why Saying No Strengthens Marketing Operations
• (13:48) - How to Decide When to Push Back
• (18:03) - Hill To Die On
• (20:03) - How to Handle Constant Pushback
• (29:55) - Wishlist
• (37:06) - How to Use Asynchronous Communication to Reduce Stress
• (44:24) - How To Evaluate Martech Tools Based On Real Business Impact
• (48:45) - Why Marketing Ops Needs Visible Work Systems
• (51:24) - Health Awareness
• (52:56) - How to Recognize and Prevent Burnout in Marketing Operations

Summary: Anna built systems to keep marketing running smoothly, but the real lesson came when those same systems failed to protect her. In this episode, she shares how saying no became her survival skill, why visibility is the antidote to burnout, and how calm structure (not constant hustle) keeps teams sharp and human. It’s a story about boundaries, balance, and learning to lead without losing yourself.

About Alma

Anna Leary is the Director of Marketing Operations at Alma, where she builds scalable systems that help marketing teams work smarter. With a focus on lead flow, data architecture, and enablement, she’s known for creating centers of excellence that turn fragmented operations into cohesive, measurable programs. As a Marketo Certified Solutions Architect and Marketo Measure (Bizible) specialist, Anna brings a rare balance of technical depth and strategic clarity to every initiative she leads.

Before joining Alma, Anna spent more than a decade shaping marketing operations strategies for brands like Uber, Teamwork, Sauce Labs, and Bitly. Whether optimizing attribution models or training teams to adopt new workflows, Anna’s work always centers on efficiency, empowerment, and driving impact across the full marketing ecosystem.

Burnout and Balance

Marketing ops work demands constant precision. Teams juggle system integrations, data cleanups, and new tech rollouts, often all before lunch. The job requires mental endurance and a tolerance for chaos. Anna understands this well. “Everyone’s trying to be the person who knows the newest tech,” she said. “It’s hard to keep up, and that adds to the mental load.” The competition to stay relevant has turned into a quiet stress test that too many operators fail without noticing.

The strange part is that ops teams often create systems designed to protect their organizations but rarely use those same systems to protect themselves. Anna explained how Service Level Agreements (SLAs) can lose their meaning when teams treat them as flexible. Urgent requests push through, exceptions pile up, and structure dissolves. Each “quick favor” chips away at the purpose of having defined processes. She put it plainly:

“If we’re making an exception for everything, then we’re not respecting the process.”

When teams stop respecting their own boundaries, burnout follows quickly. SLAs exist to create stability, and stability is what keeps people sane. Following process is not bureaucracy; it is protection. It gives operators time to think clearly, plan ahead, and make fewer reactive decisions. That way you can build predictability into your week instead of letting other people’s emergencies define it.

Anna also shared how her team reworked its entire planning system to reduce stress. “We used to do quarterly capacity planning,” she said, “but half the projects fell apart by week four.” She scrapped the process and replaced it with smaller, rolling cycles that fit the unpredictable nature of marketing requests. For someone who identifies as Type A, letting go of that much structure felt risky, but the tradeoff was worth it. Her team now works with more energy, less anxiety, and a better sense of control.

“Giving up some of that control is actually good in the end because it’s less stressful.”

Her story shows how burnout prevention depends on structure that adapts. Ops professionals do their best work when their systems reflect real life, not an idealized version of it. Boundaries, planning, and discipline should support humans, not box them in.

Key takeaway: Protect your team’s mental health by enforcing the systems you build. Treat SLAs as promises, not preferences. Review your planning cycles regularly and adjust them to match the actual pace of work. Stability in ops comes from building rules that people respect and structures that evolve as the business changes.

The Power of No

Saying no is one of the hardest and most necessary skills in marketing operations. Every week brings a new request, a “quick fix,” or a last-minute idea that someone swears will only take five minutes. Anna treats these moments as boundary checks. They test whether her team can protect their focus without losing trust or influence across the company.

“Boundaries in your personal life mirror boundaries in your professional life. You can’t sustain either without learning to say no.”

Anna connects this discipline to mental health. After years of therapy, she learned that setting boundaries preserves energy and prevents resentment from creeping into work. In marketing ops, that means understanding when to say no and why. A no can be temporary, like “no for now,” or conditional, like “come back once X, Y, and Z are ready.” That clarity gives teams space to plan properly instead of reacting in chaos.

Too many ops teams still act like order-takers. They manage tickets, fix errors, and scramble to meet every demand, even when requests come without context. Anna believes teams must reposition themselves as strategic partners. That means asking sharper questions such as, “How does this connect to our business goals?” or “Which KPI does this move?” Every yes should come with evidence, not obligation. When ops speaks in the language of impact, their boundaries start to hold.

To back that up, Anna recommends showing the work already in motion. Pull up your team’s Notion or Asana board, point to the commitments everyone approved, and remind stakeholders that priorities are already locked for this sprint. That way you can shift the conversation from emotion to logic. Plans exist for a reason. If the company wants to keep changing direction, it must accept the cost of constant interruption.

Anna’s approach creates psychological safety for her team. She recently told a contractor to stop overthinking a request that was technically impossible. Her words were simple: “It’s okay to tell them we can’t do this.” Those six words carried permission to rest, to stop chasing unrealistic expectations, and to respect the limits of their tools and time. Teams that learn this kind of confidence avoid burnout and deliver better results with less noise.

Key takeaway: Boundaries are an operational discipline, not an act of defiance. Use clear priorities, visible sprint boards, and company KPIs as your guardrails. Frame every no around impact and alignment. That way you can protect focus, maintain trust with stakeholders, and keep your team mentally healthy while still driving the business forward.

Hiring Experts Only to Tell Them What to Do

Every marketing ops professional eventually faces a request that makes their skin crawl. For Anna, it was the “no-reply” email debate. A stakeholder wanted to send a campaign from a no-reply address in Marketo. She had explained countless times why that idea goes against every principle of customer experience. It blocks responses, damages trust, and kills engagemen...