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Regional Account Executive (Midwest)
- Insight Global (Stamford, CT)
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Job Description
Key Responsibilities
One opening will be covering Great Lakes -> Must live in OH, MI, IN, IL, or WI
One opening will be covering the Central Plains -> Must live in MN, KS, or MO
Develop and execute a territory plan to identify, target, and win high-value prospects.
Consistently prospect and generate new opportunities through cold outreach, networking, referrals, and industry events.
Manage the full sales cycle from lead qualification to contract negotiation and closing.
Conduct client meetings, presentations, and proposals with executive-level decision-makers.
Build and maintain long-term relationships with clients to expand opportunities and maximize account growth – true “hunting and farming.”
Collaborate with marketing, operations, and customer success to ensure smooth client onboarding and delivery.
Maintain accurate and up-to-date records in CRM, including pipeline activity, forecasting, and account details.
Deliver timely and accurate revenue forecasts, ensuring visibility into deal progression and territory performance.
Travel regularly (2–3 days per week after ramp period) to meet with clients in person, balancing time in the field with administrative and pipeline management.
Represent the company with professionalism and executive presence at all times.
Experience & Background
5+ years of proven sales experience in B2B or service-based industries.
Experience in hunting and full-cycle sales (mandatory).
Closing of multi-million-dollar deals is a plus.
Background in waste management or related industries is preferred but not required.
4-year college degree required.
Consistent track record of achieving or exceeding quotas in competitive markets.
Experience managing territory-based sales with regular client-facing travel.
Work hours: 8:30-5:00pm, with expectation of being flexible outside of core hours for critical team events, trainings, and client engagements.
Knowledge & Skills
Strong understanding of consultative, solution-based, and value-driven sales approaches.
Ability to manage complex, long-cycle deals (typically $2.5M+).
Knowledge of territory management and client development strategies.
Strong business and financial acumen to structure deals and position the WHK value proposition.
Familiarity with CRM systems for pipeline management, forecasting, and reporting.
We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to [email protected] learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.
Skills and Requirements
5+ years of proven sales experience in B2B or service-based industries
Experience hunting and full cycle sales, mandatory
Closing of multi-million dollar deals is a plus
Background in waste management or related industries is a plus, but not required
4 year college degree is required
Track record of consistently achieving/exceeding quotas in competitive markets
Experience managing territory-based sales with regular client-facing travel Success Parameters (KPIs/Metrics)
New Business Acquisition – securing net-new clients within assigned territory.
Revenue Growth (Annual Contract Value) – delivering consistent, sustainable revenue.
Deal Size – ability to drive and close $2.5M+ opportunities.
Client Engagement – high frequency and quality of client-facing meetings each week.
Quota Attainment – achieving or exceeding monthly, quarterly and annual sales targets.
Sales Cycle Efficiency & Pipeline Health – disciplined progression of opportunities and accurate forecasting.
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We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal employment opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment without regard to race, color, ethnicity, religion,sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military oruniformed service member status, or any other status or characteristic protected by applicable laws, regulations, andordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or the recruiting process, please send a request to [email protected].
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