Sr. Manager of Sales Development - $200K to $210K OTE - Transportation Management SaaS - Chicago (In-Office) - Equity

RevsUp represents a privately-held vertical SaaS company that was founded in 2020 and has already powered billions of dollars in trucking revenue.

This 108-employee, Series B firm (nearly $50 million total funding), which has earned a 4.9/5 rating across 47 G2 reviews, is hiring a Sr. Manager of Sales Development to serve as the #2 leader in Sales Development, develop frontline managers, accelerate SDR ramp time, and scale a high-performing outbound organization. This is a Chicago-based role working in-office 4 to 5 days per week with no travel required.

Solution

A modern, end-to-end transportation management SaaS platform purpose-built for asset-based trucking carriers. It brings order management, planning, dispatch, invoicing, driver pay, financial reporting, and other critical workflows into one easy-to-use system, helping carriers replace spreadsheets, paper, and disconnected legacy tools while moving more loads and operating more efficiently.

The customer impact is tangible. Crapo LTD reduced its backlog of unbilled loads from roughly 3,000 to below 500, enabled same-day invoicing, and estimates the platform saves its operations manager 10 to 15 hours per week. Humboldt Pacific reports that billing is now 30% faster.

Role

• Expansion leadership hire reporting to the Head of Sales Development, and working closely with the CRO and Co-Founder. The Sr. Manager will be the consistent #2 leader for an SDR organization of approximately 30 reps, with 2 team leads and 3 frontline managers.
• $140K to $160K base, $200K to $210K OTE, plus equity. Quarterly bonuses, comprehensive medical, dental and vision coverage, unlimited PTO, and a 401(k) through Empower round out the comp plan.
• Highly hands-on leadership role: coach and develop managers, listen to cold calls, provide specific coaching directly to ICs, diagnose performance problems, and build systematic improvements that get SDRs productive faster.
• The team supports a high-velocity, outbound-heavy SaaS motion with $20K to $50K ACV and an average 2 to 3 week sales cycle, typically moving from discovery/demo to an onsite meeting to close.
• SDRs and sellers engage trucking company owners and operations leaders, often working with non-technical stakeholders at mid-market bulk commodity carriers.
• More than 90% of reps are currently hitting goal, the sales team averaged 120%+ attainment last quarter, and the lowest individual attainment was 97%.
• The larger business has grown ARR from approximately $8 million to more than $14 million, representing 70%+ growth, with a target of $17 million+ by year-end.
• This hire gets to coach the coaches and reshape how a nearly 30-person SDR organization ramps and performs, with management development, cold-call coaching, and proactive problem solving explicitly identified as priorities for the next phase of growth.

Culture

• The company has a 4.7/5 Glassdoor rating, with 84% of reviewers recommending the company to a friend and a 100% positive business outlook. One employee writes: “I've had so much opportunity for career growth at a growing business working with really amazing people.”
• The company currently holds a 4.9/5 G2 rating across 47 reviews, with 97% of ratings at five stars. One verified G2 user says the platform is “extremely user friendly and makes the load and billing process more manageable.”
• The Founder and CEO previously held management and investing roles, earned his MBA from Stanford Graduate School of Business, and is also a Partner at Investment Group of Santa Barbara. In 2026, he joined the board of publicly traded vertical SaaS company AppFolio.
• The company completed its Series B in September 2025, bringing total funding to nearly $50 million. The company was incubated at Investment Group of Santa Barbara and is backed by IGSB, Partners Fund, Altos Ventures, and Waybury Capital. The Series B was oversubscribed by existing investors without the company seeking outside capital.

Headquarters: Chicago, IL 60606

Total Employees: 108

Official Job Description

About the Role

Sales Development plays a critical role in the company’s growth across the U.S. In this role, you’ll lead a growing team of outbound SDRs responsible for targeting, engaging, qualifying, and scheduling meetings with high-potential customers. We’re looking for a leader who can design, implement, and manage strategies that generate pipeline and help achieve quarterly sales targets.

You’ll also be instrumental in developing a strong team culture, providing mentorship and coaching that prepares your team for future roles within the company. This position reports to the Head of Sales Development and will lead team members on the Sales Development Team. The role is based in our downtown Chicago HQ and can expect to be in office 5 days a week.

You’re excited because you will…

• Build and Grow a High-Performing Team

You’ll be responsible for sourcing, interviewing, and hiring top SDR talent to scale the team. You’ll continuously assess strengths and opportunities within the team to provide tailored management and targeted coaching.

• Drive Strategic Sales Performance and Regional Collaboration

You’ll actively support front-line SDRs, ensuring quality prospecting activity, providing coaching for success, and assisting on strategic opportunities. You’ll also integrate SDR efforts with sales goals to drive alignment and measurable results.

• Lead with Empathy and Effective Communication

You’ll foster a positive, performance-driven team environment in a high-volume, fast-paced setting, acting as a supportive leader who inspires, challenges, and motivates.

• Contribute to the company’s Growth and Culture

You’ll be a key driver in expanding our market presence and will model the company’s values of thinking longterm, focusing on our customers, empowering great people, and directly influencing the company’s success in the transportation management space.

Why Join Us?

At the company, we believe in empowering our people and fostering a supportive, innovative environment. When you join us, you'll find:

A Culture of Growth: We invest in our employees' professional development, offering mentorship, learning opportunities, and clear paths for advancement within our rapidly expanding company

Meaningful Impact: Be part of a team that's genuinely transforming the trucking industry with cutting-edge technology, directly contributing to our customers' success and our collective growth

Comprehensive Benefits:

• Comprehensive medical, dental, and vision coverage to support your well-being
• Unlimited PTO to ensure work-life balance and provide flexibility
• 401(k) policy managed by Empower to help you plan for your future
• Gym membership
• Vibrant Chicago HQ: Work from our dynamic downtown Chicago office, collaborating with a passionate and driven team.

The company is an Equal Opportunity Employer. The company provides equal employment opportunities to all employees and applicants without regard to race, color, gender (including pregnancy), religion, national origin, ancestry, disability, age, sexual orientation, gender identity or expression, marital status, language, ancestry, genetic information, veteran and/or military status or any other group status protected by federal or local law. If you require reasonable accommodation for the application and/or interview process, please notify a representative of the Human Resources Department.