Mike Cleghorn
Enterprise Account Executive
Toronto,ON
Summary
Highly motivated Enterprise Account Executive with a proven track record of 7 years in software sales. Expert in navigating complex sales cycles and building meaningful client relationships, consistently surpassing sales targets.
Overview
8
8
years of professional experience
4
4
years of post-secondary education
Work History
Enterprise Account Executive
SysAid Technologies
08.2023 - Current
- Managed all enterprise opportunities in North America, playing a pivotal role in shaping the strategic direction and growth of the enterprise segment.
- Instrumental in the development and evolution of the enterprise team. Led a comprehensive restructuring of the sales process, including the refinement of pricing models, enhancement of BDR support, and the formalization of key sales documents and procedures such as proposals, business cases, and RFP processes.
- Achieved a significant milestone by closing the second-largest deal in 2023, valued at $123k, with a multi-billion dollar organization, demonstrating exceptional negotiation skills and business acumen.
- Developed a 1.7m pipeline for 2024.
- Currently the closed 86K this calendar year.
Account Executive
SysAid Technologies
03.2023 - 08.2023
- Managed all outbound mid-market opportunities across North America.
- Demonstrated agility and competency by quickly onboarding and securing a new customer within the first quarter of engagement.
- Effectively ran complete sales cycles, from initial booked meetings to final contract signatures, showcasing strong end-to-end sales process management skills.
- Independently conducted comprehensive product demonstrations without the assistance of a Sales Engineer, highlighting a deep understanding of the product.
- Exceeded sales targets in the first two quarters, achieving $82k against a goal of $75k, leading to a promotion to the role of Enterprise Account Executive.
Mid Market Account Executive
Vena Solutions
11.2020 - Current
- 83% to plan over 2 years selling in the Mid-Market segment. 750k in total ARR.
- Work cross functionally with my sales development team to accelerate generation of new opportunities through issue resolution and new sales tactics
- Produced self generated pipeline opportunities through LinkedIn, calling and emails
- Helped onboard new Regional Sales Managers
- Certified to demo Vena platform
- Trained in MEDDIC
SMB Account Executive
Vena Solutions
07.2019 - 10.2020
- 2020 Presidents Club (150% to annual quota). 253k closed in ARR
- Top performing Area Sales Manager (SMB Segment)
- Helped develop and create new workstreams for our SMB segment by working cross functionally with different departments
- Managed partner sales channels along side sales development
Business Development Representative
Vena Solutions
03.2018 - 07.2019
- 2019 Presidents Club for achieving 125% of quota
- Top performing BDR in 2019
- Generated quality pipeline opportunities
- Developed new prospecting strategies (LinkedIn, email & calling)
Associate Account Executive
Yelp Wifi
04.2017 - 03.2018
- Managed full sales cycle
- Helped develop new sales processes post acquisition
- Trained new reps and yelp employees on the Turnstyle product
- Executed 100+ cold calls per day alongside managing existing sales cycles
Business Development Manager
Turnstyle Solutions
07.2016 - 04.2017
- Learned all new sales systems (Salesforce and Outreach)
- First BDR at the company - created all new workstreams alongside manager
- Set up effective cadences and cold call scripts
- Consistently achieved quota
- Contributed to the company being acquired by Yelp for 30m
- Experience going through acquisition process
Education
Bachelor of Arts - Political Science
Bishop's University
Quebec 09.2012 - 04.2016
Skills
Proficient in Salesforce, Zoominfo, Seismic, Uberflip, Outreach, Salesloft, Workday, Linkedin Nav, Gong, 6sense and CAPDB
Accomplishments
2024 Spirit of Sales Award at SysAid (Award for Hard Work and Dedication)
2023 Top Enterprise Sales Rep at SysAid
2020 President Club as an Area Sales Manager
2019 Presidents Club as BDR
2017 Turnstyle Acquisition
2016 Purple Letter Award - Excellence in Varsity Sports and Academics
Timeline
Enterprise Account Executive
SysAid Technologies
08.2023 - Current
Account Executive
SysAid Technologies
03.2023 - 08.2023
Mid Market Account Executive
Vena Solutions
11.2020 - Current
SMB Account Executive
Vena Solutions
07.2019 - 10.2020
Business Development Representative
Vena Solutions
03.2018 - 07.2019
Associate Account Executive
Yelp Wifi
04.2017 - 03.2018
Business Development Manager
Turnstyle Solutions
07.2016 - 04.2017
Bachelor of Arts - Political Science
Bishop's University
09.2012 - 04.2016
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