Submitted GTM Challenges From Attendees

Win Loss Week registrants submitted the most pressing go-to-market challenges they currently face for the panel to answer and provide ideas and advice.

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Anna Fisher
Chief Marketing Officer

Anna is a results-oriented marketing leader with a proven track-record building integrated marketing organizations by blending brand strategy and demand generation. Prior to joining Spiff, Anna served as the Vice President of Marketing at ZoomInfo where she led lead generation, brand awareness, product marketing, and customer marketing. Anna is currently based in Boston where she lives with her husband and 3 children.

Saber Sherrard
bain & company

Saber is a Global B2B Marketing Capability Leader and leader in Commercial Excellence with over 15 years of consulting experience focused on technology and industrial companies. He has extensive experience in driving growth via integrated sales and marketing disciplines including demand generation and sales play design. Most recently, Saber led GTM transformation including route to market design, sales play system install and ABM program launch.

Michael Tuso
Chief Executive Officer

Michael Tuso is the Co-Founder and CEO of Callypso, a software platform that helps companies with net revenue retention. Prior to co-founding his current company, Michael served as the Director of Revenue Performance and first sales leader at Chili Piper, scaling through a $650m valuation. Michael is a two-time honoree of the American Association of Inside Sales Professionals Top 25 Leaders to follow list, has been named the Sales Development Leader of the Year by Tenbound, and has been listed as a top sales leader to follow by Crunchbase. Michael has spent his entire professional career in sales and has worked for a Fortune 500 company and brand new startups alike. He is very passionate about go-to-market strategy, sales, and building startups.

Toby McGraw
Senior Vice President of Sales

Toby McGraw has nearly two decades of experience growing and scaling successful technology startups with a focus on innovation and efficiency in the transportation industry. He joined HopSkipDrive to lead sales in 2018 and rapidly expanded the company across the United States to nearly 20 different markets in 12 states.  Toby deeply cares about educational outcomes and wants to remove barriers to success by optimizing student transportation. Thanks to his efforts, HopSkipDrive partners with many of the largest school districts across the country to support the most vulnerable student populations, including students with special needs, those in foster care, or students experiencing homelessness. 

Prior to HopSkipDrive, Toby led the sales team at Zonar Systems which was acquired in 2016 by Continental AG. He worked with the company while they scaled from $5M to $150M in ARR. Prior to leading the entire sales organization, he built and led many individual teams including Field Sales, Inside Sales, Sales Development, Sales Engineering, and Sales Analytics.

John Mayfield

John Mayfield is a general partner at Album VC Prior to Album, John was an early employee at Qualtrics and pre-IPO Instructure. While there he worked in sales, marketing, and new product launches. Preceding those two companies, John spent several years in Silicon Valley working on M&A valuations for top software companies such as Oracle, HP, Yahoo, Cisco, and Amazon.

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