Profile
Jessica Gilmartin

Jessica Gilmartin

Chief Marketing Officer, Calendly

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Jessica Gilmartin
Jessica Gilmartin
Calendly Chief Marketing OfficerAugust 19
The most important thing around influence is clearly identifying and communicating how your work is contributing to sales success and ultimately having a positive impact on the business. Early on in my career, I learned that the most effective marketers are deeply committed to designing their goals around metrics sales teams actually care about. This essential insight is what inspired me to shift away from measuring leads to measuring marketing-generated pipeline. Changing metrics may be daunting at first but it’s ok to be uncomfortable. In my experience, it’s the best way to move away from a dynamic where marketing and sales blame other teams for standing in the way of their success. If you see this dynamic bubble up, consider it an invitation to reframe your work in the context of finding shared metrics that ladder up to a larger company goal. By measuring your success with metrics both stakeholders actually care about, you’re laying the foundation for a trusted partnership that has the potential to drive tremendous growth for your business. When you have that trusted partnership, the sales team should feel really excited about your roadmap and be asking how they can get more support because they find your work so valuable to them. This is a great opportunity for you to jointly present for additional resources - having sales and marketing both make the same budget or headcount request is much more powerful than marketing doing it alone.
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Jessica Gilmartin
Jessica Gilmartin
Calendly Chief Marketing OfficerAugust 19
I love this question. When you’re a small company, the stakeholders are a pretty small group: You’ll work with a small number of sales reps who generally serve similar customer groups and operate using the same sales strategy. As a result, the type of demand gen work you have to do is generally pretty consistent and straightforward (not that it’s easy!). As companies grow, customer bases expand and evolve, making Demand Generation work increasingly complex. For example, companies will begin serving additional geographies, each of which require their own programs. On top of that, sales reps will sell into new customer segments, which adds another layer of segmentation to consider. When a company shifts from private to public, we start to have conversations with even more stakeholders, including investors, analysts or perhaps your company’s board of directors. To tackle the complexity that comes with a growing business and also evade the temptation of doing everything, prioritize the programs that are the most scalable and will help make the company most successful as a whole. Communication is also essential: The big thing I teach my team is to never say no to sales (it feels draining and demoralizing to always say no, since we all know sales is always clamoring for more support). Instead, say yes AND agree on which program you will deprioritize as a result of adding the newly requested one. In other words, make program prioritization a shared responsibility. As a marketer, our job is to work with sales and understand which programs we can jointly drive to make an impact together.
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Jessica Gilmartin
Jessica Gilmartin
Calendly Chief Marketing OfficerAugust 19
This is a tricky one! First, you should assume that both stakeholders have good intent and that they’re willing to work together to resolve the issue. It’s critical to go in with a positive mindset! Then, try to create a shared fact base so that you’re all working from the same data. Once you have a shared understanding of the facts, then you can begin to build shared goals. Ask lots of questions to find shared goals between the stakeholders, and help them work towards a compromise that meets both of their goals (or at least as many of their goals as possible!)
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Jessica Gilmartin
Jessica Gilmartin
Calendly Chief Marketing OfficerAugust 19
I treat my cross-functional partners as if they’re my customers. So, I spend most of my 1/1 time with them learning about what they care most about, what key challenges they face, and the goals they are working towards. If I need their help, I always ground our conversation in how their support will help us both achieve a common goal. If I can’t find a common goal, then I know I have two options: Figure out who else in the organization does have that goal (and get them involved) or change the scope of my project so that they are willing to help. It all comes down to listening with empathy and always taking a step back to consider: What is best for the company and how does it contribute to our shared mission? Sometimes, taking that step back can reveal that prioritizing projects other than mine may even be the right thing to do.
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Jessica Gilmartin
Jessica Gilmartin
Calendly Chief Marketing OfficerAugust 19
We care a lot about clarity, both for our customers and our internal teams. So it’s important for us to build clarity into every step of the planning process: * First, we align on goals: We don’t start any project until the team is aligned on the project’s goals and how they ultimately ladder up to our company’s key objectives and mission. On an individual and team level, goals help everyone understand why their work matters and what they should be working towards. * Next, we answer the big questions: We create a clear project brief and set up a kick-off meeting including key stakeholders, always pointing back to the project’s objective and how it’s moving the business forward. * Then, we figure out who’s on first: Once we’ve agreed on the brief and the goals, then we assign tasks and owners (in Asana of course!). The project owner’s job is to hold everyone on the team accountable for their deadlines and deliverables. With distributed/remote/hybrid teams, every decision and action item has to be written down and agreed to ahead of time. Finally, we communicate with urgency and purpose: The project owner’s role is to constantly check in with key stakeholders on progress, report out regular updates to the team (usually monthly at the beginning of a project, and weekly or even daily as the deadline approaches), and help reshuffle timelines and scope if workloads and priorities change.
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Jessica Gilmartin
Jessica Gilmartin
Calendly Chief Marketing OfficerAugust 19
No matter where I am in my career, I always consider my work in the context of how I’m making the company more successful in achieving its goals. In other words, rather than focusing on my personal priorities, I spend my time thinking about how the problems I am solving show up across the organization, and how I can partner with key stakeholders to solve them. As a marketer, our challenge is often understanding how our work supports sales. I learned early on in my career that partnering closely with SDRs and AEs will make my team more effective and the company better. So I make sure to build strong relationships with the sales teams (at every level, from our Head of Sales down to individual reps) so that we build trust and connection right away. I also ensure that my team co-creates the marketing roadmap with sales so that we feel like equal partners. By putting the work in up-front to build trust and relationships, when it’s time to influence the sales team (who I definitely don’t have authority over) they are more willing to listen and act because they know I’m coming from a place of shared goals, respect, and empathy for their needs.
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Credentials & Highlights
Chief Marketing Officer at Calendly
Top Demand Generation Mentor List
Demand Generation AMA Contributor
Knows About Influencing without Authority