From Sales to Marketing: Nicole Penland's First 100 Days as Demand Gen Director

Nicole Penland started in sales, moved into marketing on the strength of a campaign idea she pitched directly to a senior VP, and recently finished her first 100 days as Director of Demand Generation at Reciprocity. She recently completed her first 100 days as Director of Demand Generation at Reciprocity, a San Francisco-based SaaS firm providing risk and compliance solutions to organizations of all sizes.

Previously, while in sales at Symantec, her successful “Campaign in a Box” ideas earned recognition and generated enough sales leads to significantly boost the revenue pipeline. A problem she identified inspired Nicole's lateral shift from insider sales to marketing.

‍I wasn’t getting what we needed and there were things I wanted to solve.

She decided to address the problem herself, pitched her ideas to the senior VP, who gave her the lead marketing role.

Moving from sales to marketing wasn't a step sideways—it gave Nicole a direct line to understanding what actually moves buyers. That context shapes how she builds campaigns now.

Nicole's path—from sales rep to award-winning demand gen director—offers a repeatable model for anyone navigating that same transition. In this conversation with the UserGems team, Nicole breaks down how she structures her first 100 days, finds the right mentors, and consistently creates leverage from a sales background in marketing roles.

Be proactive and set goals

Nicole's edge comes from moving first—identifying problems before anyone assigns them to her and pitching solutions directly to leadership. This strategy worked well for her at Symantec and everywhere since.

She accelerates her success in the first 100 days of any new job or transition by breaking it down into 30, 60, and 90-day periods – each with its own goals, milestones, and timelines to achieve them.

She sums up her blueprint for success as:

“Have a mixture of short and long-term goals potentially. Here's what I think we should go after and solve quickly, and here are the long-term goals. In the back of my head, what are the mission and the vision for us as an organization and making sure that those are still aligned.”

Michael Watkins book, The First 90 Days, is her recommendation to anyone looking for a deep dive into strategic planning in the initial days of any endeavor.

She always plots her goals and the organization’s goals on paper and identifies key areas where she can have the most impact. “There is something to be said for finding quick wins to show your value right away.” But, on the other hand, be mindful to gather as many facts and internal nuances in the beginning before jumping to conclusions.

Find the right mentors

‍Find people who believe in you and can back you up.

Good mentors give you honest feedback, open doors, and help you pressure-test ideas before you bring them to leadership. That's the practical value—beyond the obvious network access.

“It goes both ways,” says Nicole. “I've been approached by someone who wants to be mentored, and then I've identified other people that I've seen that I just enjoyed working with, and I thought, I think it can be a mutually beneficial relationship. Here's the thing. It doesn't have to be a director. Mentoring an individual, contributor mentors, can come at all different levels within the organization.”

What matters is the match and what each person gets out of it.

For Nicole, she feels a responsibility to mentor the next generation of marketers and sales reps. "One of my greatest achievements is the success that my teams, people that have worked with me or under me, when I see them succeed and move up and on and get to where they want to go. To me, that's the real measure of impact.”

People first, always

Culture determines execution speed. Nicole has seen teams with strong products fail because the people running them weren't aligned or bought in—and she's seen the reverse too.

Nicole’s experience working for large and small companies has been equally valuable, but she always emphasizes the company’s mission and its openness to diversity of ideas.

“We've done some things, previously, at Symantec that we're bringing to Reciprocity that I'm very excited about – something called the Innovation Lab. It's bringing different people from different parts of the organization together to talk about innovation.”

Cross-functional diversity—different roles, backgrounds, and contexts—consistently produces ideas that homogenous teams miss.

Sales to marketing advice

Transitioning from sales to marketing was an easy shift for Nicole. In marketing, a sales background gives you immediate credibility with the sales team and a sharper instinct for what buyers actually need.

She summarizes some of the invaluable lessons learned in a lateral move that ended up identifying new strengths and reshaping her career. This marketing advice applies whether you're a sales rep considering a pivot or already mid-transition.

• Before you shift from sales to marketing, find the industry you’re passionate about and then learn and read everything about it. Understand the key trends in that industry.
• Start in sales. Anyone wanting a marketing career should try sales first. There are more opportunities in sales, especially at the entry-level.
• Sales experience builds instant credibility with the sales team. You deal with sales from a place of empathy, having learned what it’s like to make 100 calls per day.
• Sales gives you one-to-one customer interaction and understanding of their struggles. In a marketing career, it’s critical to stay current on what impacts the customer and how to solve their problems.
• Always be your best and advocate for yourself.
• Know when it’s time to move on and take the next step in your career. Nicole says, “I know I'm ready when I'm not being challenged in my current position. And I find something that I am more excited and maybe passionate about going out to solve.”

For more great information and the full interview, be sure to tune in to: "The First 100 Days of Switching from Sales to Marketing with Nicole Penland, Reciprocity"