Trent Dressel

Deel

Account Executive

CourseCareers

Course Instructor

Qualtrics

Tech Sales Instructor

If you're interested in starting a career in tech sales, I'm the instructor at CourseCareers where I put together the most in depth course teaching people how to break into tech sales without a degree or previous experience required. You can use this link to start the free introduction course if you want to learn more: https://coursecareers.com/trentdressel

Culture Amp

Lead Account Executive - Enterprise 

Chicago SHRM

Bite Size HR Podcast Co-Host

Assist in developing and acting on Chicago SHRM's strategic plan and serving as an ambassador to connect and communicate the value to our current members.

Board Member

I serve as a strategic partner and advisor to HR leaders and their teams to help design best-in-class employee experience programs on our experience management platform. By implementing an "always-on" continuous listening program, we focus on key topics such as DE&I, employee productivity & engagement, candidate experience, and L&D to surface insights and prescribe actions to help them attract, develop and retain top talent.

Strategic Accounts Executive | Employee Experience (EX)

Senior Account Executive | Employee Experience (EX)

Chicago Better Business Bureau

I led our business development strategy to include Customer Success, SMB, Enterprise and Inbound sales teams. My team and I worked with businesses every day, educating them on how to increase trust and credibility with their customers by managing their reputation online through our Accreditation program. Chicago BBB experienced six consecutive years of growth and ranked 7th out of 99 BBBs in total new sales (11,196) and 9th in total account growth (1550+).

Held dual role as Assistant to the President and eventually Chief of Staff to collaborate with and serve as an advisor to the CEO and senior team to lead our strategic planning and organizational culture and employee experience transformation. Key initiatives included: engagement surveys, candidate experience, new hire onboarding and training, performance management, compensation plans, leadership development to include implementing Gallup Strengths, and career pathing.

Vice President of Business Development & Chief of Staff (Strategy & Culture)

Director of Sales/Assistant to the President

Tribune Company

Successfully manage all internal and external SMB outbound sales teams to include: Recruitment, Retail, Lead Generation, Membership Sales, Online Listings and forsalebyowner.com.  Focus on increasing market share in all our markets while maximizing new business opportunities.  Responsible for overall growth of the outbound teams by evaluating sales reports, metrics and working closely with operations to streamline business procedures and increase efficiency.  Provide reporting and analysis of outbound performance to both internal and external clients.  Collaborate on sales strategy to coincide with areas of opportunity.  Managed complete reorganization of retail advertising tele-sales team including compensation, metrics, territory reassignment and lead strategy

Director, Outbound Sales-SMB

Responsible for directly managing, motivating and mentoring outbound advertising sales teams.  Assisted in the development of sales strategies and analyzed results to determine future strategies.  Created and implemented project plans to successfully launch new outbound projects for internal and external clients to include: Lead Generation, Daily Deals, B to B membership and Athletic Ticket Sales.

Sales Manager

Chicago Tribune Media Group

Managed and directed all aspects of an inbound call center.  Implemented and reviewed call center policies and procedures.  Motivated sales reps to achieve high performance, monitored calls for quality assurance and handled escalated calls that fall outside the purview of supervisors.

Sales Manager-Advertising Contact Center

With a background in Industrial/Organizational Psychology I have spent years partnering with HR and People Teams across industries to help design end-to-end employee listening strategies - from onboarding to exit, and every moment that matters in between. 

For me, employee experience isn't just about measurement - it's about creating a continuous conversation between employees and the business. It's about helping leaders take action on what matters most and making sure employees feel heard, valued, and empowered to do their best work. 

Because when you get employee experience right, everything else improves. Culture, performance, retention, innovation, and customer experience. 

I’m also an active member of the HR community. I serve on the board of Chicago SHRM, where I’ve contributed to strategic planning efforts that provide resources, networking opportunities, and support for HR professionals across Chicagoland. I created and host for them the Bite Size HR Podcast, where I interview HR leaders and industry experts on a wide range of topics.

Outside of work, I’m a husband, father to two amazing kids, and the youngest of eight siblings.

I’m also passionate about pickleball. This sport has not only become a favorite pastime but also a way to build incredible friendships and connections. Fueled by this passion, I created CrossKourt Pickleball, a brand dedicated to celebrating the people, stories, and organizations that make the pickleball community special. Through CrossKourt, I share my journey in the sport, highlight those making an impact, and host exciting cash tournaments.

Whether you’re interested in discussing Employee Experience, getting involved with Chicago SHRM, podcasting, or talking all things pickleball, I’d love to connect!

taplio

The Battle

Trent Dressel

Frank Laterza

Followers

Posts

Engagements

Likes

Ready to grow your LinkedIn presence?