From ‘Pick Your Brain’ to Thriving Business with Ashley Rudolph

Ashley Rudolph is no stranger to requests to “pick her brain.” 

Throughout her career as a senior operations executive, Ashley took informal consulting calls with people who wanted her insights on the ed tech industry. When the 2023 tech downturn put her at an unexpected inflection point in her career, Ashley decided to turn those “pick your brain” requests into a business. 

Today, Work With Ashley R. offers coaching and consulting services to help individuals grow their careers and founders grow their businesses. Ashley’s 2-pronged business model reflects her expertise as both an operations expert who has successfully scaled several businesses and a leader who knows how to develop people. 

Here’s how Ashley has translated her career journey into a thriving independent consulting business. 

From IC to VP: Ashley’s journey up the corporate ladder

After a few years in nonprofit marketing, Ashley knew it wasn’t the path for her. She was interested in startups, so she started networking in the New York tech scene, where she met people who worked for General Assembly — then a 3-year-old startup in the emerging Edtech space. 

Ashley took a pay cut and a demotion to join General Assembly. “I wanted to be in tech really badly, and I believed in GA as a company,” she explains. “So I just jumped into it.” Soon, she was managing back-end web development and data science courses, hiring data scientists and Ruby on Rails engineers. 

She realized quickly that General Assembly needed to accelerate scaling the program experience. “We shouldn’t be winging it,” she recalls thinking as she embarked on an effort to create a formula for scaling technical courses.

“I did that for my program, and the leadership team saw what I was doing and promoted me into overseeing all the programs across all locations,” Ashley says. Later, she took over General Assembly’s financing programs. Just 4 years after she entered the tech world as an individual contributor, she was running consumer operations and reporting to the COO.

Turning a downturn into a pivot

“GA was like an MBA for me,” Ashley explains. She parlayed her experience into a similar role scaling events for another Edtech company, then transitioned into a VP role leading product operations. 

Then the 2023 downturn hit — and Ashley’s entire division was cut. 

“There was something in me that realized I don’t just want to jump into another job,” she says. She’d always been intrigued by the possibility of going solo, and the layoff was the push she needed to pursue an independent career. 

But this wasn’t Ashley’s first foray into consulting. “All throughout my time at General Assembly and the other startups I was at, I would get calls from people who saw me as an expert in the ed tech industry,” she explains. The fact that she’d gotten paid for her insights before gave her the confidence to take the leap into entrepreneurship. 

How Ashley’s career path became her business model

Work With Ashley R. offers services that map to Ashley’s background as an operator and a leader of teams and people. 

“As a coach, I’m someone’s copilot for the time that we’re working together,” she explains. Some clients come to her as inbound leads, but she also partners with founders, CEOs, or Heads of HR who want her to coach their team members. 

She leverages her own experience as an operator at startups to help emerging operations leaders make decisions confidently and navigate tough situations: “I’m equipping them with the skills to be their best at whatever level they end up being.” 

Her approach combines strategic frameworks — helping people think broadly about being a good manager and leader — with tactical guidance. 

“I want you to focus on the big picture,” she says, but achieving long-term goals requires solving short-term problems, whether that’s resolving conflict with a colleague or managing a difficult employee. “I have done this. I can help you navigate those conversations so you’re coming to them more informed.” 

For her consulting clients, she fills a short-term operations skills gap. “They need me for a short period of time because they have a problem or a question,” she says. Most of her clients are founders trying to break into Edtech or grow a startup from 0 to 1. They lean on her for advice on a wide range of topics, from Edtech go to market strategies to team structures. 

Iterating toward an offering

Ashley spends roughly 75% of her time on coaching and 25% on consulting — the opposite of what she expected when she started out.

Feedback from her network helped her land on the right offering. “I thought people were going to want to hire me to do operations projects,” Ashley says, but she kept hearing that people wanted a full-time or fractional operations leader to embed for the long term, not a consultant. 

She discovered that people wanted to leverage her expertise in a different way. “They valued the fact that I had actual experience at startups,” she says. “They valued my experience as a good manager and leader. People were drawn to the fact that I was able to climb a ladder and go from an individual contributor up to a VP.” 

Today, she works primarily as a performance coach, and she’s happy to have settled on this model. “I’m learning so much about myself and how I work and how others work,” she says. 

Never underestimate the power of your network

Ashley’s top advice for anyone embarking on an independent career is to harness the power of your network. “I wish I would have done it sooner,” she says. 

Connecting with people from across her career — some of whom she hadn’t spoken to in years — helped her refine her business model and led her to clients. “Even if you think that it’s been too long, do it anyway,” she suggests. “You never know what’s going to come out of it.” 

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