TextExpander – Account Executive
Notable
Results
- SaaS/B2B account executive closing deals in a large to global enterprise pipeline, working with C-level and other executives in a wide range of verticals.
- Concurrently managed a faster-paced Mid-Market pipeline for the first year, displaying the ability for managing a high volume of activities and deals through strong organization skills.
- Managed the full, complex (not transactional) sales cycle, including Account Mapping, Outbound, Lead Qualification, Discovery, Demo, Business Case and POC, Multithreading, Negotiation, and Closing.
- Developed ~60% of my pipeline through creative, multipronged outbound.
- Led ITSec, Legal, and Procurement negotiations.
- Represented Sales in the HubSpot conversion project.
- Presented with the “Most Positive Person” in the company award at the 2023 company offsite.
- 2022: 134% of quota.
- 2023: 155% of quota (quota doubled from prior year).
- 2024: 124% of quota YTD (quota grew 50% from prior).
- Closed more than 400 deals over the past two years.
- All of the above were #1 rankings on the team.
- Drove Average ARR per deal from approximately $1,600 when I arrived to over $45,000.
- Landed the biggest deal ($287,600) in company history, approximately 3X the previous record.
- “Broke into” and closed 2 deals with a major tech company that had previously been impenetrable.
SAMPLE DEAL LISTING:
The deals shown in the tab ln the table to the right are not a comprehensive list and were not chosen exclusively based on deal size. Instead, there’s a unique, instructive storhy to each. It will give you a sense of what I’ve been working on. (The $1 million deal was at isidore). September 2021 to Present
The Isidore Group – Senior Account Executive
Noteable
Results
- Senior Account Executive selling managed IT, cybersecurity, and other technology and phone services to mid-market and large Chicago companies using highly consultative, solution selling and value based selling approaches.
- Responsible for all lead generation and full sales cycle activities.
- Worked effectively with C-level and other executives through complex sales cycles.
May 2020 – September 2021
- Produced 592% of quota.
- #1 ranking on the team.
- Largest deal (~$1,065,000) in company history.
- The record-setting deal started with cold outreach to the CEO based on market signals. After a series of discussions, he agreed to a cybersecurity overhaul and full IT audit.
- He insisted on involving his executive team (right out of Challenger).
- I eventually met with 19 C-level and other executives to gain consensus.
- The deal closed with a phone call late on Friday night following a presentation to the entire executive team of about 40 people in their huge conference room.
- The initial deal was about $665,000. I added another $400,000 for phone system overhaul and other items during installation of the initial sale.
The significance of the deal outlined above is how it demonstrates my effectiveness in a classic complex sales cycle, from the creation of the lead through effective outbound, to C-level discussion starting with the CEO and then multithreading downward through other high-level segments of the organization, the final presentation and then closing.
Gembrook Software/ClubExpress – Senior Account Executive
Notable
Results
- Sold association management software to groups and associations with member counts of up to 10,000 or more, predominantly using a value-based selling approach.
- I was assigned the entire “Villages” (V-to-V Network) program, a wonderful non-profit program that helped seniors age gracefully in their home, supported by ClubExpress to this day.
- Mentored others on the team, reviewing communications, sitting in on sales calls and giving advice afterward, documenting, revising, and teaching sales processes.
March 2019 to May 2020
- Closed 156% of quota, the #1 ranking on the team.
- Closed the most deals on the team.
Bullnbear Financial – Registered Investment Advisor/Owner
Notable
Results
- Left my Citi VP role to start an independant registered investment advisory practice (a start-up!) offering investment management and comprehensive financial planning services mostly to the affluent, including executives and business owners.
- Routinely closed deals in the $5-10 million range en route to building assets under management of well over $200 million.
- Recruited, coached, and managed a team of as many as ten individual producers (in addition to my personal production) and related support staff.
- In true start-up mode, this meant I was in charge of portfolio management, trading accounts, all staff administration, technology setup, website building, and everything else!
- Engineered a successful exit with a very profitable sale of the business in 2018.
February 2002 to October 2018
- Routinely landed in the Top 1% of producers in a broker dealer of approximately 1,375 producers.
- Routinely qualified for the “Circle of Excellence” and “Founders Club” (both are like President’s clubs).
- Very proud of the highly successful sale of the business.
Citicorp – Operations VP / Regional Sales Manager
Notable
- As a part of the “Fast Track” program, held both high-level sales management and operations management positions.
- Cross-functional performance led to promotion to VP.
SALES
- Led a team of 8 account executives for the southeast US region, leading the company in production for both years.
- Flew to home office monthly for about two years to teach SPIN sales training classes to new account executives from across the country, even though I was still in Operations at the time.
OPERATIONS
- Managed a Regional Operations Center with as many as 89 people.
- Used Production Dynamics methodologies to redesign operations workflows which cut mortgage processing times by 75%. The success of the program led to my promotion to VP and transfer to home office.
- I flew around the country to other regional centers to install my programs.
- Managed the building of the National Originations System, from definition of standard processes and best practices, development of system requirements, managing the team of consultants that built the system, and rolling it out nationwide.