This episode features an interview with Jen Dimas, CMO of Gigster. For more than 20 years, Jen has led marketing teams at high-growth enterprise software companies like Plex, Demandbase, Egnyte, Polycom and Hyperion.

In the episode, Jen dives into the ever-changing landscape of demand gen strategy, highlighting the importance of understanding and adapting to the needs of the moment. She also emphasizes the importance of a tight partnership between sales and marketing, and explains how to go about cultivating it.

• Which tactics and technologies are best for empowering digital-first, adaptable marketing teams
• How to align sales and marketing teams across performance, strategies, and goal setting
• Why measuring everything from first touch to close is essential to marketing’s success

“As in all things marketing, ‘it depends’ is always the answer. There's not a demand gen strategy that is consistently applied that would make any sense. You have to understand your situation and adapt to whatever the needs are and the resources available in that moment.”

"I need to partner tightly with sales. I just don't believe that sales and marketing exist as separate functions from each other. They're all connected and a part of driving customer value and bookings and revenue...That relationship with the head of sales, next to my relationship with my boss, is my most primary relationship at work. It's something that has to be strong so that we're doing the best job we can for the company.”

“You need to have enough trust in the relationship of the executive team that you can have healthy conflict. That is the goal of having a healthy executive team. When there is conflict, I always consider it a sign of health, as long as it's respectful conflict and you're saying things in the best interest of the business, even things that are hard, that's the goal, right? You want to have a conversation where you can say hard things.”

“Your website is your always-on front door, and that needs to reflect your corporate positioning–what is your value to prospects and customers–but it also needs to engage folks from a demand perspective and speak to investors and potential employees, so it’s very, very important.”

“Do not try to make decisions about change in a vacuum. Leverage your community. Talk to marketers who've made the same kinds of decisions or faced the same challenges. Talk to salespeople who have struggled. Leverage people with experience because they're out there, and there's no need to reinvent things that have worked and a lot can be learned from other people's successes and mistakes.”

(1:44) Moving from Marketing Ops to Demand Gen

• Jen started her career in marketing operations
• Realized that she didn’t enjoy doing the same thing over and over, and that she needed a new challenge
• Her CMO at the time (Heidi Mulin, who we recently hosted on a previous episode!) gave her the opportunity to run the North America field marketing team at Polycom
• She’s never looked back; she loves the challenge and she loves being able to work closely with sales
  

(4:08) How Jen Approaches Demand Gen Strategy

• As with most of marketing, the answer is “it depends”
• There isn’t one demand gen strategy that can be consistently applied; you must understand your situation and adapt to the needs and resources of the moment
• Generally, she looks at revenue targets first, determines the necessary pipeline to hit those targets, and then builds a journey for specific target personas across awareness, close, retention, and upsell
  

(5:24) How Jen Structures a Marketing Team

• Demand Gen: includes Marketing Operations and often an SDR function
• Brand & Creative Services: website, PR, influencer marketing, corporate communications
• Product Marketing
  

(10:39) Gigster’s Strategy for Engaging a Buying Committee

• Gigster offers both a service and a product, and the buying committee for each of those can be unique
• Their challenge lies in the fact that there isn’t a clear title that consistently owns the decision-making process — it’s the person in charge of digital transformation, but that can live in many different parts of an organization
• They use qualifying questions to understand how digital transformation is handled within an organization and to scope which executive oversees it
  

(17:02) How to Cultivate a Great Sales-Marketing Relationship

• Jen doesn’t believe sales and marketing are distinct functions — they need to be connecting and drive customer value and revenue together
• She loves to sit down with sales leadership to define joint objectives and plan together
• Her relationship with the head of sales is comparable to her relationship with her boss as her most primary relationship at work
  

(18:24) Creating Demand for Gigster’s Talent Network

• Jen also oversees creating engagement within Gigsters Talent Network, the “gig” workers behind Gigster’s offering
• This is similar to a B2C motion
• Jen’s goal is to create a sense of community and capture their stories to explain their benefit to future customers
  

(21:35) Jen’s Three Uncuttable Budget Items

• Sales and marketing alignment: This is a non-negotiable; it must always be present and invested in. This is a “budget” item in a unique sense in that it requires time investment.
• Transactional selling system: For Jen, this is usually Salesforce and Marketo
• Website: This is your “always on” front door. It needs to reflect your corporate positioning, but also engage visitors to create demand
  

(24:42) Launching New Corporate Positioning

• When Jen joined Gigster, there wasn’t consistent positioning used across the company
• She aligned with the CPO and launched a full corporate positioning exercise
• The previous website was very hard to understand and had a ton of inconsistent content
• They replaced the website with a thinned-down site that told their new story very clearly
• Over time, they’ve been adding more content across the website
• Currently working on making the website even more engaging now that they have clear messaging adoption across all pages
  

(27:35) Jen’s Favorite Demand Gen Campaign

• One of her favorite integrated marketing campaigns was one she was involved with at Plex: the product marketing team created a book about how to evolve manufacturing with cloud-based technology. 
• The book became the focal point of a major brand and outreach campaign; they built demand activities across multiple quarters around certain sections of the book
• Coordinated across sales and marketing to create a conversation that was impactful for the business
  

(29:38) Jen’s Biggest Learning Campaign

• While growing the enterprise motion at Flex, they thought a specific persona was involved in influencing decisions
• Put a ton of focus on engaging that persona, and it was successful — they generated a lot of conversations with this persona they hadn’t been able to do previously
• As they measured progress, they realized this persona wasn’t able to drive deals forward and were not the influencers they thought they would be
• Jen’s learning: always monitor and measure! If they only looked at first-touch measurement, they would have thought the campaign was successful. It was critical that they looked deeper in the funnel, they realized the true impact wasn’t there
  

(31:47) Why Jen Co-Founded Women in Revenue

• Jen is a founding member of the Women in Revenue organization, created for women in marketing, sales, and customer success roles
• Made up of 3,000 members, and they host quarterly events as well as a mentorship program
• Half of the organization is comprised of people advanced in their career, and the other half are people coming up in their careers
• Goal of the organization is to create a place for conversation to help everyone move forward
  

(33:55) Marketing Trends Jen is Most Excited About

• Jen’s very interested in the discussion around how important MQLs are; should we used form gates to capture leads, or does that create too much friction?
• Also very interested in new technologies that allow us to understand so much more about the buying journey and digital footprint of prospects
  

(37:31) Quick Hits: Getting to Know Jen

• New shelter-in-place hobby: Jigsaw puzzles, Cribbage, and a new (third!) dog
• Alternative career: Would love to make a career out of mentorship
• Advice for a CMO: Leverage your network! You’re not the first person experiencing your challenge. There’s a lot to be learned from other people’s successes and mistakes.