From Tech Support to SVP: Karen Ainley's 'Squiggly' Path to Product Leadership

Karen Ainley, Head of the Accountants Business Unit at Sage, has achieved a remarkable milestone: 29 years with the company. Her career trajectory is a testament to the power of seizing opportunities, staying authentic, and the changing landscape of gender and career development in the tech industry for women.

Pioneering Women in Tech and Fostering Cultural Balance

Karen's tenure at Sage started back in 1996 with a pioneering programme designed to support women returning to work after having children on a part-time basis. She notes that the commitment to a balanced culture has only grown more critical over time.

"I think it's great that we give new people, or people coming up through the ranks, confidence that as a woman they can succeed in this organisation, they can succeed in tech and that they can become leaders in product."

She views gender balance as a business imperative, especially as the industry moves into the world of AI and generative accounting. A diverse and balanced culture, not only in gender but also in age demographic is essential for building the best products for customers.

Mentoring and Overcoming Barriers: A Product Champion's Role

As a leader and a champion for our Thrive in Product career acceleration program, Karen sees her role as a blend of mentoring and instilling confidence in women who are new to or looking to enter tech. She draws on her own extensive experience, acknowledging the unique barriers women can face in a historically male-dominated industry.

In her early move into product management, working closely with engineering teams in the late 90’s, Karen faced a stark reality:

"It was dominated by men... leading to constant imposter syndrome for me. At one point, I even got told by a male leader that, you know, I wouldn't get anywhere in this business because I was too open, too honest, too authentic."

Karen’s response was definitive: she stayed true to herself. She credits her success to remaining true to her values and emphasises that "playing games" are not requirements for leadership at Sage. She emphasises this point to apprentices and graduates: anyone with ability and determination can succeed at Sage.

A Career Built on Opportunity and Change

Karen’s longevity at Sage is rooted in the constant pace of change and the diverse opportunities that have arisen for her. She didn't start in tech; she began her career in accountancy, before taking a break to have her son.

Her career path has been a "squiggly," moving from support into training, pre-sales, sales, product training, and product marketing. This breadth of experience gave her a crucial, all-around grounding in how the entire business works to develop and take products to market.

"The thing that's kept me here for 29 years is the pace of change, but also the opportunities that have arisen for me over those 29 years."

Having started her career without a university degree, instead completing an equivalent to a modern apprenticeship, Karen is proof that there is no single, prescribed path to the top. She stresses that anything is possible if you remain determined and true to your values.

The Essential Skills for Tech Success

While admitting that resilience and sheer tenacity were once key for women navigating the industry, Karen believes the skills for thriving in tech today are universal:

1. Excellent Communication: Essential for alignment across product, design, and engineering teams.
2. Influencing Skills: Critical for driving your project forward in a large organisation where you rely on other business units.
3. Building and Fostering Relationships: Underpinned by trust, this is the foundation for effective teamwork.

For anyone starting their career or looking to break into tech after a career break, Karen’s final advice is to foster a passion for what you do, and to constantly seek to understand the customer.

"Nothing is ever sold just in the office. Get out there, speak to customers, learn from customers. The customer doesn't always know what they want. They think they know what they want, but actually they're relying on you as a product expert to take them that next step further."