How to Win in your Career: From Finding the Right Fit to Making Your Mark

Topics we will discuss include:

  • How to determine the best fit?
  • Nailing the job interview.
  • Onboarding in a new role.
  • Habits that can hold you back.
  • Personal Brand/Vision and what you want to be known for.
  • How to find the right resources to advance in your career.
  • Personal stories from leading women in FinTech.


Stefanie Mockler, Consultant, Vantage Leadership Consulting

Stefanie Mockler is an organizational psychologist and leadership coach whose mission is to identify and develop strong leaders. She has supported her clients through critical role transitions and onboarding into new positions, and worked with high potentials to accelerate learning and growth. Some of her most fulfilling engagements have involved helping women recognize their edge and step into their power as leaders.

As a young mother and ambitious career professional herself, Stefanie experienced firsthand some of the challenges that women tend to face, particularly in male-dominated fields. To continue to bridge the gender divide and help women rise into leadership roles, Stefanie founded The Female Leader’s Edge. Her mission is to create inclusive, flexible, and family-friendly organizations that promote viewing people as not simply employees, but whole people with lives and interests outside of work. Her insights have been featured in HR People + Strategy, Society for Women Engineers Magazine, Vantage Point Blog, and on her personal site.

Diana Toscas, Sr. Engineering Manager, Braintree Payments

Diana Toscas is a Senior Engineering Manager at Braintree. Diana joined Braintree in January 2018 to lead their platform app teams. In June 2019 Diana took a new role at Braintree under the Acquiring Solutions team to lead Merchant Search and Reporting Solutions Engineering teams.

Prior to joining Braintree in January 2018, Diana worked at CME Group for 15 years. She started her career at CME Group in 2001 as an API Support Specialist. By 2008 Diana was promoted into Engineering Management and led teams within the platform and product space.

Diana’s early years in FinTech were difficult and lonely; she did not have any mentors or guidance from anyone who could relate to her background. Nonetheless, through hard work, focus, and resourcefulness, Diana progressed to become Senior Director at CME Group. Today, Diana is very passionate about helping women and underrepresented groups in tech realize their potential; she has mentored many Finance or Tech professionals.

Diana was born and raised in Chicago in the Belmont-Cragin neighborhood. After attending high school in Arecibo, Puerto Rico, she returned to Chicago to obtain a degree in Computer Science from Loyola University Chicago. Diana, who is of Puerto Rican and Honduran heritage, is a first generation college graduate in her family. Currently, Diana lives in the Lincoln Square neighborhood in Chicago with her partner and two kids. She enjoys nature, time off with her family, skiing, reading, and going for long walks.

Rumi Morales, Partner, Outlier Ventures

An early specialist in digital currency, blockchain and distributed ledger technologies, Rumi is also a leading early investor in artificial intelligence, deep learning, predictive analytics, and quantum computing as they will affect traditional industries.

A proven entrepreneur herself, Rumi established the Global Markets Institute during her tenure at Goldman Sachs and also launched a leading economic research firm in Singapore. She began her career in venture capital in London, Kuala Lumpur, and New York, and has invested across three continents and lived in seven countries.

Currently based in Chicago, Illinois, Rumi is actively involved in that city’s burgeoning technology and entrepreneurial community.

An accomplished and dynamic public speaker, Rumi has presented onstage at major conferences globally and has been featured on Bloomberg Television and Institutional Investor magazine. Institutional Investor also noted her as one the “most powerful dealmakers in financial technology” two years in a row, and Crain’s recognized her in their esteemed “40 Under 40” list.

Rumi received her undergraduate degree from Wellesley College where she was elected to Phi Beta Kappa and received her MBA from the NYU Stern School of Business.

Carrie Compston, HR Professional

Carrie has always been passionate about her career. As a Human Resources leader, she brings nearly 20 years’ experience helping businesses to leverage talent and culture as a strategic advantage. She’s equally as passionate about being a great mom and role model to her two children (now 10 and 7) and understands the tough decisions ambitious women face balancing personal and professional commitments. Carrie encourages women to identify and protect what’s most important to ensure trade-offs are in their favor.

Women in FinTech Initiative (WIFI) Team

Kimberly H. Wolfson, Founder, Women in FinTech Initiative; IT Consultant, Hook Strategies

Growing up in a family dedicated to improving lives and livelihoods, Kimberly inherited the desire to make a positive impact on the world. As the Founder of Women in FinTech Initiative (WIFI), she, along with the WIFI team, is redefining what it means to be a female innovator in FinTech, through education, meaningful engagement, and social impact. As an Information Technology and Customer Success Manager, Kimberly’s passion and discipline for technology, data, and innovation has enabled her to design, implement, and support transformative customer solutions that have driven growth and efficiency for companies such as Grant Thornton LLP, Discover Financial Services, OfficeMax, Beam Global Spirits and Wine, ConAgra Foods, and Papa John’s Pizza. Kimberly graduated with a Bachelors of Science in Speech in Marketing Communications & Advertising from Emerson College in Boston Massachusetts.

Kathy Krzeptowski-Sabala, Senior Consultant, Northern Trust Corporation

Kathy Krzeptowski-Sabala is a Senior Consultant at Northern Trust Alternative Fund Services who provides 3rd party administrative services to Hedge Fund’s and Private Equity firms. She has managed several of the worlds largest asset managers globally currently on the Northern Trust’s Omnium Technology platform and has been active in engaging internal partners in the fintech community by leading the FinTech Leaders program, along with actively participating in the Women in Leadership for further expansion.

Kathy believes in the next generation fintech technology that will impact the current legacy platforms behind the world’s largest financial services firms. Through assisting Kim Wolfson with the Women in FinTech Initiative and involvement at Northern Trust Fintech Leaders program, Kathy has expanded herself to be forward thinking and passionate female intrapreneur to help financial service firms engage themselves in the fintech community. Kathy holds a Bachelor of Science in Finance from DePaul University.

Debbie Zaller, Principal, Schellman & Company, LLC

Debbie has worked within the IT industry for the past 20 years. She is no stranger to issues women face within male-dominated fields. Throughout her career, she has had several mentors the supported her in this challenging environment, many of which she still works with as a Principal at Schellman & Company, LLC. In fact, Debbie was the first female Principal at Schellman & Company. She strives to help younger women overcome the same challenges and empower women with leadership, knowledge and expertise.

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