Her Story
About Karen
Karen Howe is a Boston, Massachusetts-based sales professional with 23 years of experience in sales overall and 12 years specifically in software sales. She began her career in financial services at Wells Fargo Financial right out of college, drawing from a strong familial background of salespeople and entrepreneurs, before transitioning into software, where her passion lies in analytics, automation, and artificial intelligence. Throughout her career, including nearly five years at Alessa prior to its acquisition and her subsequent layoff, Howe has demonstrated success as a top performer in diverse environments, from mature companies to startups. She brings global enterprise sales experience, engaging stakeholders across departments and proving ROI for intangible software solutions. Howe values ownership and client relationships, always positioning herself as a partner in her clients' success. She advises working smarter rather than harder and encourages young women entering tech sales not to be intimidated, noting the industry's growth and its potential to solve real-world problems efficiently.
Her Interview
Ten minutes with Karen
01What do you attribute your success to?
I would say my ability to be successful in every environment that I work in, whether it's a mature company, whether it's a startup with no customers, case studies, or references. I'm passionate about my work, and I'm also passionate about being a partner in my clients' success and bringing good sales in to the companies I work for. So, I would say passion, motivation, and also intelligence, because you really do need intelligence when you're selling high-tech software.
02What’s the best career advice you’ve ever received?
Work smarter, not harder. You'd be surprised how many people don't follow that. In sales, you could spend all your time reaching out to the people that aren't decision makers, or you could spend time reaching out to people that could actually make a decision to buy your software.
03What advice would you give to young women entering your industry?
I would say don't be afraid to keep trying, and don't be intimidated. There are a lot more women in software sales even now, than there was back in 2014. It's a great industry to be in, and not be intimidated to keep going after it. Tech is fascinating, and it solves real-world problems, and the right kind of software can just make a company's operations a lot more efficient.
04What are the biggest challenges or opportunities in your field right now?
From a competitive standpoint, there's always gonna be a lot of different software companies in various stages of product development. Sometimes software companies could be selling software that's not fully developed, or is developed, but not working properly. So really making sure to dispel reservations in selling your software solution, that it can do what you purport it to do.
05What values are most important to you in your work and personal life?
I would say ownership. So, taking responsibility for what you do, and also the client relationship, and always being the face of the company for your clients, even when they might be having issues with other departments. Truly being a partner in my client's success and wanting all of my clients to succeed.
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