Roger Benson

SVP, Head of Sales - Email

2023 - Current

The Customer Communications Cloud Integrate messaging, voice, or email capabilities into your tech stack and maximize opportunities across the customer journey — with unmatched scalability, deliverability, and cost-effectiveness.

Advisor

2022

Sometimes all you need is 60 seconds. The quickest way to meet with anyone. Host a live Q&A with thousands of fans, run an efficient town hall with your direct reports, or ask your coworker a quick question.

Limited Partner

2021

The California Innovation Fund powers a cycle of education, innovation, and entrepreneurship to make VC more equitable and create impactful positive change.

VP, Sales

2022 - 2023

The Apple Device Management and Security Platform -Responsible for all North American Enterprise and Commercial Sales teams --Headcount: 3 Directors, 9 Managers, 6 Enterprise AEs, 50 Commercial AEs, 20 SDRs --ACV: $15,000, Largest Deal: Alliant $160,000 ARR, $320,000 TCV --Monthly ARR Impact: +$2m -Partnered with executive team to refine GTM strategy and optimize team personnel, business systems and processes in order to scale the business to $100m+ -Hired, trained and developed a team of Front and Second-line Sales Leaders, AEs and BDRs -Worked cross-functionally with Heads of Partnerships, Customer Success and Revenue Operations to develop, implement and ensure adoption of GTM systems including accurate reporting, forecasting, territory creation and lead assignments --Metrics Impacted: outbound activity, pipeline creation, time to close, average deal size, annual recurring revenue

VP, Growth & Mid Market

2021 - 2022

1-click checkout without passwords - anywhere. -Tasked with moving an existing team upmarket through strategic hiring and intensive sales development in order to target mid-cap and lower-enterprise accounts <$100m -Worked cross-functionally with sales ops and strategy teams to develop ideal customer profiles and deploy regional territories to maximize coverage -Increased average size of merchants closed won from <$100k annual online GMV to more than $25m -Consistently executed new business on a monthly basis providing ground cover while our upper-enterprise and strategic sales cycles progressed -Successfully onboarded more than 200 net new Growth-sized merchants adding more than $500m in committed GMV to Fast -Singularly recognized amongst my peers with an “above and beyond” award for performance beyond the scope of my assigned role and responsibilities

VP, SME

2020 - 2021

-Hired to build and scale a high-velocity outbound sales team to target small and medium sized business operating at <$1m annual online GMV -Aggressively expanded headcount from 4 to 16 AEs while accelerating per rep productivity and overall team output -Successfully onboarded and activated more than 1000 new SME merchants with Fast Checkout in just 4 months

Division VP, Mid Market & Emerging Enterprise

2018 - 2020

Yelp connects people with great local businesses. -Responsible for leading Mid-Market & Emerging Enterprise Sales @ Yelp: serving primarily regional and small national businesses across multiple verticals - a highly performant team including an RVP, 3 RDs, 12 Managers and 150+ ICs in sales and account management across the country -Successfully accelerated growth on historically slow-moving $11m annual revenue line in 2017 – scaled aggressively to exit 2019 at $79m ARR -Delivered consistent growth Q/Q every quarter for more than 2 years -More than doubled AOV from $24k to $50k by redesigning account assignment/distribution strategies using a combination of 3rd party data and internal AI/ML models to identify top opportunities -Improved retention, reduced setup errors, and increased budget fulfillment by co-authoring an aligned sales/customer success framework to streamline the customer journey and highlighting opportunities for campaign optimization -Deployed a functioning demand-gen engine in partnership with marketing projected to account for 20% of total MM revenue in its first year of operation -Worked closely with internal, cross-functional leadership at all levels including engineering, product, operations, as well as learning and development

Regional VP, National

2017 - 2018

-Responsible for Enterprise & Mid-Market sales in the Eastern US region -Oversaw all acquisition sales and account expansion with a dotted line to regional customer success and revenue operations -Owned a direct reporting relationship with the senior-most AEs in the region including the top earning sales rep in the company ($1m+ gross commissions in FY'17 -- notable clients include Staples, Subway and Target) -Drove consistent growth in-region including consecutive quarters as the top-performing region in the org (1Q18->2Q18)

Director, SMB Sales

2014 - 2017

-Responsible for an organization of 12 local sales teams with a headcount of 120+ -Developed a daily repeatable management playbook deployed org-wide -Goaled at $30m+ in annual booked revenue -FY2016: achieved 127% of assigned quota -FY2015: achieved 105% of assigned quota -FY2014: achieved 107% of assigned quota -Presidents Club Attendee 2015, 2016, 2017 -Highly sought after for mentoring and career development coaching

Senior Manager, Sales

2011 - 2013

-Responsible for leading a team of 12 local AEs carrying a monthly quota of ~$300k in booked revenue -Closely managed sales activities to acquire new accounts and exceed targets -Barged 4+ hours of sales calls daily to assist in capturing revenue opportunities -Charged with recruiting, hiring and training all acquisition sellers in NY -FY2013: achieved 117% of assigned quota -FY2012: achieved 116% of assigned quota -Presidents Club Qualifier 2012, 2013

Account Executive, Local Sales

2010 - 2011

-An entry-level, high-output, cold call sales job focused on hyper-local SMB -Tasked to aggressively grow customer base and increase penetration into high-value market segments by exceeding monthly $20k quota targets -Worked across all verticals and in several key local regions (East Harlem, Williamsburg and Jersey City) -Presidents Club Qualifier 2011

Valuations/Operations Analyst

2007 - 2008