James Koursaris
Naperville,IL
Summary
Dynamic sales leader with a proven track record in driving large-scale Enterprise sales as well as targeted startup PODs. Expertise in revenue growth and customer base expansion, complemented by strong skills in solution selling and relationship building. Recognized for consistently surpassing sales quotas through exceptional deal closing, leveraging sales methodologies, and team motivation while ensuring sustained market development. Career objectives include further enhancing leadership capabilities while fostering innovative sales strategies.
Overview
20
20
years of professional experience
1
1
Certification
Work History
Vice President of Sales
Windstream Enterprise
Chicago, IL
02.2023 - 02.2025
- Leading a growing customer base of $348M in ARR, driving aggressive expansion of the current install base, and new logo acquisition—focusing on QoQ growth, customer experience, and solution diversity.
- Leading a sales and revenue organization with a headcount of 65, encompassing Direct Sales, Customer Success, Sales Engineering, and Channel Management for Windstream Enterprise off-net business.
- Grew enterprise portfolio business from $219M to $348M ARR, achieving a 58% YoY increase through strategic enterprise sales and operational initiatives.
- Presidents Club - 2023, 2024
- Established ambitious goals for employees to promote achievement and surpass business targets.
- Lead learning and development initiatives to educate sales personnel on new products and services.
- Collaborating with marketing teams to develop and implement promotional strategies and campaigns.
- Aligning sales objectives with business initiatives using strategic development, forecasting, and budgeting - Achieving an average of 97% forecasting accuracy from BOM to EOM.
Vice President Of Sales
SeoClarity, LLC
Chicago, IL
09.2021 - 02.2023
- Leading a global sales team of 2 Sales Directors, 8 Senior AEs, (6 in US, 2 in EMEA), 6 BDRs
- Guide Sales Directors on KPI / Performance attainment
- Manage full P/L for Sales Operations, Training, T/E, and Technology Enablement
- Negotiate contracts and propose creative contract offerings to help sales staff close competitive deals
- Analyze competitive environment and customer procurement trends to support growth strategies
- Team Quota of $12.0M
- Set baseline expectations for outbound BDR performance and conversion expectations
- Implemented and managing MEDDICC Methodology with proven results in shortened sales cycles, increased deal sizes, and conversion rates
- Data Driven KPI integration to day-to-day leadership
- Number of value driving activities to deal close
- Built Data Analytics dashboarding for KPI monitoring
- Continued Coaching and performance growth implementation
- Brought in 2 Enterprise F25 clients based on personal relationships into the organization within the first 60 days of hire
Senior Director Of Sales And Business Partnerships
Within3 Software
08.2019 - 08.2021
- New Logo Acquisition - Player Coach
- Lead team of 4 AEs, as well as individual Quota
- Team quota of $10M
- Source new opportunities to fuel Within3 Insights Platform
- Annual Quota of $1.5M, Average Deal Size - $250k, average sales cycle - 90-125 days
- Collaborated with marketing department personnel to optimize strategic initiatives
- Generated $1.9M in Pipeline in first 5 months with cold outreach strategies - email sequences, videos, and webinars
- 240% of Quota in 2020
- 115% of quota in 2021 before departure
Senior Director - Enterprise Sales
Jive Software, Inc.
04.2016 - 05.2020
- Annual Team Quota $43MM
- Leading 2 Enterprise Sales Managers, 20 Account Executives, BDR Team, Sales Enablement, Sales Operations
- Developed strategy for BDRs and AEs for outbound cold outreach including automation, and personal cadences
- Averaged 34% close rate on SQLs, and 54% close rate at after 'demo' stage
- President's Club Award Winner - 2017, 2018, 2019
- Global Elite Club Winner - 2018, 2019
- ICP partners: CIO, CMO, VP Operations, VP Marketing, VP SaaS Ops, VP IT Systems
- Implemented MEDDICC Checklist that was adopted by rest of sales Org globally
- Successfully lead digital transformation efforts for clients in implementing JIVE and other Aurea products
- Consultative approach to solutioning, supporting internal customers
- Excellent communication and leadership across sales, marketing, operations
Director Of Partnerships
Anju Software Solutions, Inc
01.2011 - 04.2016
- Company Overview: Medical / Life Sciences Technology SaaS, Regulatory workflow and Content Management Solutions
- Client Focused - Seeking to create partnership to create solutions for success
- Quota of 1.5M on average over 4 years
- Leveraged MEDDICC and SANDLER framework for overall 140% quota attainment throughout 4-year period
- Average deal size of $250k; average sales cycle of 90-120 days
- 3-5x pipeline with 100-150 cold calls, and around 1000-2000 personalized emails/week
- Grew team of up to 7 AEs - each with $775k - 1.0M quota and a team quota of $7.5M Annually
- Presidents Club Award Winner (2012, 13, 14, 15)
- 5 AEs (at least) received same award every year under my leadership
- Implemented Territory and Vertical specific Account Planning for new logo acquisition
- Build out MEDDICC reporting into SFDC and created score carding system for value metrics
- Establishes and reports on metrics to measure team performance; correct deficiencies where necessary and implements strategic and tactical plans to gain the most amount of revenue from client while growing the business partnership
- Medical / Life Sciences Technology SaaS, Regulatory workflow and Content Management Solutions
Senior Account Executive
Abelson-Taylor, Inc
Chicago, IL
01.2008 - 01.2011
- Quota Driven Individual Contributor with quarterly quota of $250k
- Selling Creative, Managed Services, and Professional Services to Key accounts, as well as bringing in new business
- Key part of account team and project team in providing creative and flexible solutions to make clients happy while building relationships and fulfilling business needs
- Supporting all client brand needs and collaborating with multiple teams to deliver work that excels
- Selling great creative by understanding core business strategy and brand objectives
- Manage pipeline end to end; proposals, CRM updates, contract management etc
- Identified industry trends and best practices, leveraging them appropriately to support the client strategic imperatives
- Create and Maintain project PLs as well as usage statements and cost-to-date reporting to clients and internal
- Lead strategic pitches to clients for digital solutions
- Worked with Creative, analytics, and Production teams to form presentations
Investment Analyst - Alternative Energy (ESG)
UBS Financial Services
01.2005 - 01.2008
- Gather and analyze research data related to targeted industry and companies, and maintain accurate, current research databases
- Prepare industry and company reports, presentations and exhibits to summarize research findings for Research teams
- Present to F1000 my analyses on market sectors and trends toward Energy Governance Policies (now ESG)
- Maintained business relationships with Venture Capital and small business sector energy startups as well as major Fortune 1000 clients while facilitating their product and demand needs
- Lead capital raising initiatives to reach goals of patented products to the open market
- Excellent communication skills with organized and detail oriented follow-up processes
- Capital Raise initiatives of over $100MM for alternative energy and corporate ESG Investments
- Financial Efficacy and pro-forma Model creation and presentation to clients in investment feasibility
Education
Bachelors Of Arts - Political Science
Oakland University
Bachelors Of Science - International Business Finance
Oakland University
MBA - Managerial Economics
Loyola University
ChicagoSkills
- Leading Leaders
- Sales talent acquisition
- Deal closing
- Pricing strategy
- Sales presentations
- Sales team motivation
- Sales enablement
- Revenue generation
- Sales and Market Development
- Solution Selling
- MEDDICC methodologyy
- SPIN Selling
- Salesforce Software
- Decision Making
- Sales Quota Management
- Team Recruiting and Onboarding
- Relationship Building
- Verbal and Written Communication
- Persuasive Selling
- Prospecting Skills
- Product positioning
Certification
MEDDICC Certification and Mentor
Accomplishments
- President's Club 2023, 2024
- Elite Club 2020 Award Winner
- President's Club Award Winner - 2013, 2015, 2016, 2017, 2018, 2019.
- Global Elite Club Winner - 2018, 2019
- Exceeded sales goals by average of 30% from 2013-2020
Languages
- English, Native/Bilingual
- Greek, Full Professional
Timeline
Vice President of Sales
Windstream Enterprise
02.2023 - 02.2025
Vice President Of Sales
SeoClarity, LLC
09.2021 - 02.2023
Senior Director Of Sales And Business Partnerships
Within3 Software
08.2019 - 08.2021
Senior Director - Enterprise Sales
Jive Software, Inc.
04.2016 - 05.2020
Director Of Partnerships
Anju Software Solutions, Inc
01.2011 - 04.2016
Senior Account Executive
Abelson-Taylor, Inc
01.2008 - 01.2011
Investment Analyst - Alternative Energy (ESG)
UBS Financial Services
01.2005 - 01.2008
Bachelors Of Arts - Political Science
Oakland University
Bachelors Of Science - International Business Finance
Oakland University
MBA - Managerial Economics
Loyola University
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