Pleasant Middelhof Career Change Expert | Speaker | Company Operations nerd |

Founder

Career Jump Academy

Sep 2025 - Current (1 year)

Career Jump Academy - Ready to leap into the career or role that is uniquely aligned to your strengths, interests, and lifestyle? Feeling STUCK at your current job, or blocked from advancing in your current role? Then the Career Jump Mastery Course is for you!

Expert

Primary Venture Partners

Jun 2024 - Current (2 years 3 months)

I'm excited to be a part of the Expert Advisor network at Primary. I provide strategic advice and guidance to the investment team and founders within the Primary portfolio and broader network. As an expert, I have access to early-stage businesses, emerging trends and technology, and an expanded network of exceptional leaders and resources through a top-tier seed-stage firm.

Chief Operating Officer

Operator

Apr 2024 - Jul 2025 (1 year 4 months)

As COO at Operator.ai, I’ve had my hands in everything, working with the most talented team in all areas to bring this company to life from the ground up. I’ve been building the foundation to help us scale and grow, while making sure everything runs smoothly day-to-day. My focus is on creating strong connections between teams, streamlining our processes, and ensuring we are not just launching the best product, but also doing it with operational excellence!

VP of Sales

Convertr

Aug 2023 - Mar 2024 (8 months)

Sr. Manager of Strategic Sales

RollWorks

Mar 2023 - Aug 2023 (6 months)

Manager, New Business Sales

RollWorks a division of NextRoll

Mar 2021 - Mar 2023 (2 years 1 month)

Strategic Sales

Pendoio

Sep 2018 - Mar 2021 (2 years 7 months)

Regional Vice President of Sales

Outreach

Aug 2017 - Sep 2018 (1 year 2 months)

D

Director of Enterprise Sales

May 2016 - Sep 2017 (1 year 5 months)

Enterprise Sales

Outreachio

Mar 2015 - May 2016 (1 year 3 months)

As the Enterprise Account Executive for Outreach, my role is to uncover the needs of our clients within their sales workflow, develop a plan to meet their goals and objectives, and ensure that plan is executed effectively. Outreach is the only sales communication platform that’s simply everywhere you are, helping you make your best moves faster. This powerful B2B SaaS platform automates human touch correspondence for higher quality prospecting, and seamlessly integrates with popular selling tools Salesforce, LinkedIn and Gmail. With Outreach, teams can quickly create and customize a data-driven cadence thanks to a proprietary reply detection system which tracks both manual and automated email replies to connect and delight customers--and

Instructional Solutions Category Manager

School Specialty

Jun 2013 - Mar 2015 (1 year 10 months)

Working with the highest level of school district administration, I consulted with the administrators to identify specific deficits in their programs, and delivered effective solutions to meet their needs. In this highly competitive market, I was able to establish solid relationships with key accounts and grow sales in the territory to exceed the aggressive quota. Leveraging my existing relationships and building new ones, I have penetrated into very challenging accounts and made record breaking sales.

Teacher

Frederick County Public Schools

Aug 2007 - Jun 2013 (5 years 11 months)

Pleasant Middelhof

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