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Levi Oliphant

Levi Oliphant

Sales Leadership & Coaching Innovator | Driving Growth Through Strategic Insights

Location icon Chicago, IL, USA

About

With over 25 years of expertise in sales leadership, business development, and team coaching, I specialize in transforming challenges into opportunities for growth. My innovative use of structured methodologies like IRAC equips sales teams to surpass goals and foster sustainable client relationships. By combining analytical problem-solving with people-centered leadership, I help businesses optimize performance, grow revenue, and achieve lasting success. Currently transitioning into my “second life journey,” I’m passionate about mentoring leaders and exploring opportunities that align with my love for guiding others toward their full potential.

Job Categories

Consulting
Executive Leadership
Program and Project Management

Industries

Sales
Technology
Technology Research
Leadership Development Professional Growth

Top Skills

Sales Strategy and Execution
Coaching
Mentorship
Business Development
Revenue Growth
Analytical Problem Solving
Client Advocacy
Team Leadership
Available
Clock icon
Full-time

A
Advising
C
Coaching
M
Mentoring

What I Offer

I offer a unique blend of analytical problem-solving and people-centered leadership, helping organizations and teams achieve transformative growth through innovative sales strategies and mentorship.

Sales Coaching

Empower teams with analytical tools and methodologies to drive results.

Strategic Advisory

Guide leaders in aligning sales strategies with organizational goals.

Career Transition Mentorship

Support professionals in navigating career changes by leveraging transferable skills and building confidence.

Ask Me About

Sales Coaching Frameworks
Team Leadership
Client Advocacy
Analytical Problem Solving
Sales Strategy Alignment
Business Transformation
Revenue Growth Tactics
Professional Development

Sales Team Empowerment

Description
For sales managers and leaders looking to elevate team performance through structured coaching frameworks.
Outcomes
Enhanced quota achievement, stronger team alignment, and strategic sales insights.

Leadership Coaching for Sales Professionals

Description
For aspiring or established sales leaders seeking to refine their strategic approach and leadership skills.
Outcomes
Improved decision-making, advanced problem-solving, and career growth.

Career Transition Guidance

Description
For professionals transitioning to a new role or industry, helping them identify transferable skills and build confidence in navigating change.
Outcomes
Clear career direction, personalized strategies for success, and a strengthened professional narrative.

Customized Sales Strategy Design

Description
For organizations seeking tailored solutions to unique sales challenges.
Outcomes
Optimized sales processes, increased team productivity, and measurable business growth.

Wisdom at Work

Notable Roles

Global Sales Strategy & Operations, Competitive Specialist – Gartner

Empowered sales leaders to align strategy with organizational objectives, mentoring managers and VPs to drive performance and revenue growth.

Senior Role-Based Specialist, Software Engineering Leaders

Spearheaded coaching for sales teams to leverage GenAI and digital transformation strategies, delivering impactful solutions to client challenges.

Vice President of Partnerships – Structure Events

Established sales operations from the ground up, securing major partnerships and driving rapid growth in AI, IoT, and cybersecurity verticals.

Areas of Expertise

Sales Leadership and Coaching

I excel in guiding and mentoring sales teams to exceed performance targets through structured methodologies like IRAC and proven sales strategies.

Strategic Business Development

I develop and implement scalable solutions that align with business goals, driving sustainable revenue growth while fostering meaningful client relationships.

Sales Innovation and Problem Solving

Leveraging my legal and sales background, I design unique analytical frameworks that empower teams to approach challenges with clarity, confidence, and actionable insights.

Key Achievements

IRAC-Based Sales Coaching Innovation

Developed a unique application of the IRAC methodology to sales, equipping teams with a structured framework for problem-solving and decision-making.

Transformational Leadership at Gartner

Coached and mentored over 100 sales professionals, achieving consistent quota success and strengthening team alignment across verticals

Business Development Excellence

Drove multimillion-dollar sales growth by aligning actionable strategies with client needs, resulting in measurable success and long-term partnerships.

To me wisdom is the ability to combine knowledge and experience and apply them to your life to make confident, mindful decisions

Summary of Skills

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Levi Oliphant is a member of OpenWater Group — a trusted community and platform where seasoned professionals reimagine success through shared wisdom and meaningful connections.
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