Win-Loss Stories: Highlighting Key Wins (and Losses) Throughout Your Career

Panelists experienced in winning will share some of the key moments throughout their career on both the wins and losses. They'll share what they learned, key takeaways, and do's & don'ts.

watch on-demand
John D'Agostino
Former EVP of Global Sales

John D’Agostino brings more than 30 years of experience in B2B sales. In his most recent position as the Executive Vice President of Global Sales at Qualtrics, he led sales growth from $42 million ARR to $550 million ARR. John scaled the sales team from 50 to over 1,000 people in his sales org (including technical sales and sme’s) and helped take the company from a $350 million valuation to an $8 billion acquisition by SAP. Prior to Qualtrics, D’Agostino was part of the legendary enterprise software company PTC (Parametric Technology Corporation) where he started as a sales rep and after seven promotions ran the Americas with a 375 person sales team. John was also a sales leader at Pitney Bowes for six years, and is widely recognized as an expert in go-to-market and scaling global operations for B2B companies.

Jim Steele
President of Global Strategic Customers

Jim is an accomplished business leader with a strong track record of success in building and leading multi-disciplinary sales teams in a matrixed international environment. Over the past 35 years, he has served in executive leadership and senior sales roles within the enterprise applications, revenue solutions, and data management sectors. As President of Global Strategic Customers at Salesforce, Jim’s primary focus is bringing the full power of Salesforce to its largest and most strategic customers. Prior to rejoining Salesforce, Jim serves as Yext’s Chief Revenue Officer and President. Previously he served as President and Chief Revenue Officer of, the industry’s first AI-powered predictive sales acceleration platform. Prior to joining InsideSales, Steele served at Salesforce for 12 years as Chief Customer Officer and President of Worldwide Sales and Operations where he helped grow the company from $25 million to more than $5 billion in revenue. Steele brings more than 35 years of business experience with some of the B2B tech sector’s biggest players, including Ariba and IBM.

Kat Kennedy
General Partner

Kat Kennedy is passionate about building - products, companies, and the startup ecosystem as a whole. Before joining Kickstart as a General Partner, Kat was President and CXO of Degreed, a company dedicated to changing how people develop skills, build expertise, and grow their careers. She was instrumental in driving Degreed’s growth, shaping its product and culture, and deepening its client relationships. She partnered closely with Degreed’s customers to accelerate innovation and ensure their ability to quickly reallocate talent to the most critical strategic priorities. Kat’s 15 years of operating experience give her a unique perspective as an investor - one that allows her to not only spot talented entrepreneurs from all backgrounds but also to serve as a mentor, fostering innovation through every stage of the company’s growth.

Kortney Osborne

Kortney Osborne is a passionate executive with experience in building world-class unicorns. She currently consults for companies wanting to take their brand experiences to the next level through her company K.O. Productions and has recently launched a new startup called Omu; focusing on enabling and normalizing self-care for men.  She formerly led all Marketing programs at Weave, growing the company over 330% during her time there and helping them through an IPO exit. Prior to Weave, she worked at Qualtrics where she built and oversaw the event and marketing campaign teams. Helping build that company from pre-funding to its first $8 billion dollar exit. Kortney is lover of food, her three children, her husband and Oprah (not necessarily in that order). She serves as a Board Chair for the Women's Success Center at Utah Valley University, is PTA President for Canyon View Junior High and enjoys mentoring and supporting women through their educational and professional pursuits. She also enjoys stand-up comedy and is a forever Georgetown Hoya.

Learn How to Win More.