Founders Everywhere: Katherine von Jan
Katherine von Jan (KVJ) is the co-founder & CEO of Tough Day, the smarter way to build self-reliant, high-performing teams.
Welcome to Founders Everywhere, where we highlight the incredible people behind the companies we’ve backed at Everywhere Ventures, a global pre-seed fund supported by a community of 500 founders and operators.
In most organizations, managers are the default first stop for every employee concern, but they are often overburdened, underprepared, and unequipped to provide the guidance teams need. This gap is critical, because as the saying goes, “people don’t quit jobs — they quit managers.” But, it’s also an unsustainable expectation that managers should be the sole source of support for every workplace issue. Great managers do exist. They just don’t scale. So when employees can’t rely on their managers, where do they turn? To friends or family, who offer empathy but not expertise or contextual knowledge about their organization. Problems fester.
Unaddressed, these challenges erode morale, engagement, and performance. Tough Day solves this problem by providing confidential, expert guidance and emotional support on demand to help employees proactively resolve workplace issues. This prevents small problems from escalating into crisis, and empowers both individuals and organizations to thrive.
Co-founder and CEO, Katherine von Jan (KVJ), has spent her career helping people do their best work while understanding the factors that hold them back. A pioneer in the Future of Work and emerging technologies, she applies innovative solutions to some of the most complex challenges in the workplace. Before founding Tough Day, she led innovation and incubation as Chief Strategy Officer at Salesforce, leading initiatives to transform how teams and organizations operate. She teamed up with Alberto Escarlate, CTO, who brings deep expertise in AI and software engineering, to build Tough Day’s human-positive AI platform.
What’s Tough Day’s mission?
Our mission is enabling human agency at work, augmenting managers and HR, by superpowering employees at all levels to self-manage and succeed.
What sets Tough Day apart?
Our AI Workplace Advisor, Tuffy, is for everyone, not just managers. Tuffy helps all employees navigate complexity, build productive working relationships, and perform their best by providing confidential, expert guidance and emotional support on demand. Our human-positive AI is built with expertise and knowledge from leaders in management, HR, and employment law, and customized with organizations’ wisdom, culture, policies, and processes — with a relentless focus on trust and safety for employees and employers.
It’s not about replacing humans, but empowering them to work better and smarter with confidential, expert advice on demand and agentic workflows that support your people the way a great manager should.
How does Tough Day inspire “customer love”?
We work with midsize, progressive tech and professional services firms, as well as innovative teams in enterprise tech and media. Customers, especially HR leaders, love that Tuffy handles 80% of workplace issues on-the-spot, freeing HR professionals and managers to focus on more strategic work. Customers and content partners praise our blend of rigor, partnership, and employee-centricity.
How has your background shaped you as a founder?
I’ve started five companies and worked as an “intrapreneur” inside major tech enterprises, which has given me a rare perspective on both startups and corporate innovation. Looking at things with an anthropologist’s eye has allowed me to study and solve for the human side of work at every scale.
What books, people, or ideas have inspired your approach to entrepreneurship?
I tend to draw inspiration outside traditional startup content. How Civil Wars Start by Barbara Walter has been fascinating. Her research on resilience and instability applies to leadership in any context. I also enjoyed Shoveling $h!t: A Love Story by Kass and Mike Lazerow and Venture Everywhere by Jenny Fielding, for their very human, honest, and global takes on entrepreneurship. More than anything, I’m inspired by other founders. Their stories, humor, and grit remind me why I love building startups.
Fun Fact:
We are an immigrant family. My father was born in a displaced persons camp after World War II and his Lithuanian family came to the U.S. with nothing and rebuilt their lives from scratch. Decades later, while working in Europe, I met my husband, a German who finally (after 20 years) became a U.S. citizen. So in our home, I’m a first-generation American and so are our kids.
Tough Day is also a member of the Everywhere Podcast Network. Check out their episodes here!
Listen to Mike Quinn, with Dr. Rio Xin Chen on the Venture Everywhere podcast: Boosting the Last Mile. Now on Apple & Spotify. Check out to all our past episodes here!
