Summary
Overview
Work History
Education
Skills
Websites
Languages
Timeline
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Jeffrey May

Jeffrey May

Chicago

Summary

Quota-smashing Sales Director with 10+ years of direct SaaS sales experience. Proficient in cultivating high-performing sales teams, implementing innovative processes, and enhancing internal/external client relationships. Skilled in leveraging CRM tools & digital marketing strategies to achieve unprecedented sales growth. A proven leader committed to fostering a culture of success and continuous improvement by example.

Overview

33
33
years of professional experience

Work History

Director of Sales

AMERICAS, OTRS
09.2018 - Current

Responsible for sales recruitment, initial systems training and continuous mentorship of OTRS' sales & pre-sales personnel, throughout the AMERICAS regions & Hungary.


Reporting to the COO, I provide him with accurate monthly/annual sales forecasts & deliver quarterly reports to OTRS' Executive Board.


Hired in 2018 by OTRS AG to turnaround OTRS Inc's sales situation; a subsidiary nearly $1M into debt and on the verge of shutdown. Upon my arrival, established a collaborative partnership with Marketing to create successful print/social media/networking event campaigns. Oversaw the creation of OTRS' first Business Relationship Manager (BRM) & presales engineer positions. Introduced a prospecting-focused culture to the global sales team & implemented processes in use to this day.


Earned promotion to Director of Sales within first 18 months.


Within my first year as Director, OTRS Inc recognized a 135% increase in ARR vs. the previous year. Collectively, the AMERICAS subsidiaries achieved an average 158% increase in ARR over the same period.


Under my leadership, OTRS Inc recognized it's first profitable year in 2021, with sales revenue in excess of $1.1M.


Working in close collaboration with the BRM team, OTRS Inc's attrition rate stands at 8% vs 22% in 2018.


To date, I am the top-earning salesperson in OTRS Inc's 17-year history.

Strategic Account Executive

Travel Media Group
09.2017 - 09.2018

Sold Hospitality-specific SaaS digital marketing solutions, consisting of online & print media services, custom software development & online reputation management solutions


Leveraged cold-calling, solicitation of referrals, and onsite sales calls to Property Management Company (PMC) executives at the C-suite level, within my assigned territory


Thoroughly researched each hotel within the PMC's portfolio prior, ensuring a compelling presentation, highlighting the projected ROI my services would bring


Managed the full sales cycle from acquisition through closure; performing scheduled follow-ups to identify additional upsell opportunities

National Accounts Manager

Chetu, Inc
03.2013 - 02.2017

Sold managed IT services to technology leaders within the C-suite, consisting of offshore/onshore custom software development, project management, staff augmentation, QA/testing & data backup/recovery


Built the Hospitality, Parking, Golf, Aviation, and Public Transit verticals from the ground up


Consistently exceeded monthly sales targets & routinely ranked amongst the organization's top 10% revenue-generating salespersons


Fostered long-term client relationships to enhance account retention & referral opportunities


Conducted pre-employment screening & sales training/mentorship of new sales team members

International Travel Consultant

Liberty Travel Inc
05.2007 - 11.2010

Specialized in the preparation of international flight itineraries & luxury vacation packages for business & leisure travelers


Acquired approximately 435 new clients annually during my tenure


Averaged 17% profit margin per booking, far exceeding the industry average of 8%. This, achieved by upselling my clients on supplemental services such as upgrades, excursions & travel insurance


Cultivated relationships with suppliers to secure the most competitive rates


Remained current on industry news, so as to provide expert destination knowledge & better inform client choices

Indirect Fire Infantryman

US Army
04.1995 - 03.1998

Led training exercises for junior soldiers, enhancing team cohesion and operational effectiveness.


Coordinated logistics for ammunition supply, ensuring timely availability for operational readiness.


Conducted thorough reconnaissance missions to gather intelligence and inform strategic planning.


Honorably Discharged upon completion of service

Infantry Mortarman

US Marine Corps
03.1993 - 04.1995

Operated and maintained mortars, ensuring optimal performance in diverse operational environments.


Trained junior soldiers on mortar systems and safety protocols, fostering skill development and operational readiness.


Honorably Discharged upon transfer to US Army

Education

College of DuPage
Glen Ellyn, IL
08.2000

Skills

  • Sales Management
  • Revenue Growth
  • Client Relationship Management
  • Sales Process Improvement
  • Team Leadership
  • Digital Marketing
  • CRM Proficiency
  • Prospecting and Cold Calling
  • Deal closing
  • Sales pipeline management

Languages

English
Native or Bilingual
German
Professional Working

Timeline

Director of Sales

AMERICAS, OTRS
09.2018 - Current

Strategic Account Executive

Travel Media Group
09.2017 - 09.2018

National Accounts Manager

Chetu, Inc
03.2013 - 02.2017

International Travel Consultant

Liberty Travel Inc
05.2007 - 11.2010

Indirect Fire Infantryman

US Army
04.1995 - 03.1998

Infantry Mortarman

US Marine Corps
03.1993 - 04.1995

College of DuPage