Cale BloskasConsultative B2B sales
Running full sales cycles with mid-market organizations, from first conversation to close, including standout quarters at 298% and 863% of quota.
Sales · Leadership · Technology
Cale Bloskas, Mid-Market Sales Leader
Helping organizations solve operational challenges through technology, clear communication, and trusted relationships.
Team Lead & Senior Account Executive, Mid-Market B2B Technology Lubbock, Texas
- Quota attainment, FY2026
- 136%
- Annual contract value booked
- $1M+
- Winner’s Circle ranking
- Top 5%
- Years in B2B sales
- 9+
About
From top performer to team multiplier.
I’m a Senior Account Executive and Team Lead at a connected-operations technology company, leading complex, multi-stakeholder sales with mid-market organizations across operations, safety, and fleet.
I was promoted to Team Lead within a year. Today I still carry a full quota while leading in-person training for new hires, coaching new and tenured reps on pipeline and deal strategy, and partnering with product leaders to run the first sales cycles for beta and pre-release products.
Before that, I spent seven years building a foundation in consulting, business development, insurance, and customer-experience software, which shaped how I approach problems and why I focus on long-term customer value.
What drives me is making other people better: simplifying difficult problems, earning trust, and building teams where top performers raise the standard for everyone, not just their own number.
Outside of work, I’m a husband and a dad of three, and most of my time goes to my family. I’m always learning and building something, whether that’s ham radio, woodworking, or 3D printing.
- Winner’s Circle
- Director’s Award
- Above & Beyond Award
- Top Rookie Award
- New Hire MVP
Expertise
Where I add value.
Coaching & rep development
Onboarding new sellers with clear ramp milestones, call reviews, and real-deal coaching that builds confidence and consistent habits early.
Cross-functional strategy
Partnering with product, enablement, and leadership on beta launches, go-to-market feedback, and better onboarding and sales processes.
Career
The path so far.
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2024 – Present
Team Lead & Senior Account Executive, Mid-Market
Connected operations & IoT technology
136% of quota in FY2026 with $1M+ in ACV and Winner’s Circle (top 5%). Quarters of 863%, 298%, 205% and 203% earned Top Rookie, Director’s and Above & Beyond awards. Promoted to Team Lead within a year.
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2022 – 2024
Account Executive
Customer experience software (SaaS)
Named New Hire MVP out of 180 new hires. Ranked a top-five account executive annually while mentoring new reps through one-on-ones, shadowing and coaching.
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2020 – 2022
Director of Business Development & Sales Consultant
Sales consulting
First full-time hire. Grew the client portfolio 300% during the pandemic while training and coaching sales teams at agencies across the country.
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2017 – 2020
Commercial Account Executive
Commercial insurance & risk management
Built new client relationships from the ground up and helped shape the mentorship program for entry-level sales professionals.
How I lead
Clarity. Energy. Results.
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Clarity
Clear expectations, so everyone knows where they stand, what good looks like, and what needs to improve.
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Energy
Lead from the front, celebrate wins, and coach with care while giving direct feedback when standards aren’t met.
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Results
A repeatable rhythm of one-on-ones, deal reviews, and call reviews that catches risk early and builds predictable performance.
Praise
What colleagues say.
When I joined, I struggled with imposter syndrome, but Cale stepped in with a coaching style focused on small, actionable steps and controllable wins. Because of his mentorship, I went from feeling overwhelmed to becoming the #1 rep in the organization for trials in Q3, and ultimately hitting quota.
I’ve had the opportunity to work with Cale at two companies, and I chose to follow him because I trust his leadership and judgment completely. He’s someone people genuinely want to work for.
He creates an environment where people feel supported and confident reaching out. His ability to clearly explain workflows, troubleshoot issues, and provide guidance had a huge impact on my ramp and overall confidence.
He takes strong initiative in onboarding new hires, helping them ramp quickly and feel supported from day one. Cale operates at the next level.
Connect
Let’s stay in touch.
Send a note below, email me directly, or connect with me on LinkedIn.