Sales Training & Enablement Manager

Bridge Legal; Chicago (IL); Hybrid; USD 90,000 - 130,000; Full time

Benefits offered by this job

Health benefits

Unlimited PTO

Bonus opportunities

Flexible work life balance

Career growth opportunities

Mentorship

Job summary

Qualifications

• The ideal candidate is an exceptional sales coach who develops people and improves performance.
• Experience coaching 40+ B2C sales representatives on the shop floor and remotely.
• Skilled at live coaching, call reviews, and building scalable training processes.

Responsibilities

• Coach and develop a team of 40+ B2C intake specialists through ongoing call reviews, one-on-one coaching and training.
• Partner with Operations to identify performance gaps and implement targeted coaching plans.
• Monitor conversion rates, quality scores, and customer experience to drive improvements.
• Design and implement AI-driven coaching workflows and scorecards.
• Build dashboards to help managers coach more effectively.

Skills

Sales coaching

Call coaching

AI coaching

Performance analysis

Tools

QA platforms

ChatGPT

Job description

Bridge Legal is a hyper-growth tech startup that provides an AI-powered platform to help plaintiff law firms and litigation funders streamline mass tort and personal injury casework and unlock value from legal assets. Bridge Legal’s technology transforms fragmented legal workflows into structured, scalable systems—enabling clients to move faster, reduce risk, and achieve better outcomes for those who have been injured and harmed. Through our software, we empower our law firm clients to fight for the rights of the “little guy” with AI, automation, analytics and workflow.

We pride ourselves on being at the forefront of helping provide individuals access to the legal system and bridge the justice gap by enabling law firms to use technology and AI to serve more clients than ever before.

At Bridge Legal, we believe that teamwork and collaboration are the key drivers of success. Our team is made up of talented and passionate individuals who work together to achieve our goals and deliver exceptional results. We value open communication, mutual respect, and a willingness to go above and beyond for our customers and each other. If you're looking for a supportive and collaborative work environment where your ideas and contributions are valued, we invite you to join our team.

Mission:

We’re looking for a Sales Training & Enablement Manager who is passionate about developing people, improving performance, and building high-performing sales teams. In this role, you'll partner with our Operations leadership and existing Intake Trainer to support, coach, and develop a team of 40+ B2C intake specialists who speak with prospective clients every day. Success in this role requires someone who is energized by working directly with people—providing real-time coaching, identifying performance trends, reinforcing best practices, and helping individuals continuously improve.

This is not a role for someone who simply delivers onboarding presentations and moves on. We're looking for someone who thrives on being in the business every day—listening to calls, live coaching sales representatives, developing training content, and helping managers improve team performance.

As our organization continues to grow, you'll also help modernize our training program by leveraging AI and technology to improve call monitoring, coaching, quality assurance, and the overall learning experience. AI won't replace great coaching—it will help make it more scalable, personalized, and impactful.

If you're passionate about sales, coaching, leadership, AI, and developing people—and you're excited by the opportunity to help build the best team of intake specialists in our industry,we'd love to meet you.

Your success will ultimately be measured by the performance of the sales organization—including improvements in conversion rates, quality scores, speed to proficiency for new hires, and the ongoing development of every representative on the team.

Status: (In-Office or Remote)

Outcomes:

Sales Coaching & Performance Development

• Coach and develop a team of 40+ B2C intake specialists through ongoing call reviews, one-on-one coaching and training.
• Partner with Operations leaders to identify performance gaps and implement targeted coaching plans.
• Monitor key performance metrics including conversion rates, objection handling, compliance, quality scores, and customer experience.
• Reinforce consultative sales techniques and best practices through continuous coaching.
• Deliver actionable feedback that helps representatives improve both confidence and performance.
• Conduct side-by-side coaching, call calibrations, and live feedback sessions.
• Recognize top performers while creating development plans for struggling team members.

AI Coaching Program

• Build an AI-powered coaching program that scores 100% of calls
• Design and implement AI-driven call scoring and coaching workflows.
• Partner with Operations to develop meaningful rep-facing AI scorecards.
• Identify trends in call performance and create targeted coaching plans.
• Improve AI prompts, evaluation criteria, and quality metrics over time.
• Build dashboards that help managers coach more effectively.
• Use AI insights to continuously improve training content.

Skills and Qualifications:

The ideal candidate is first and foremost an exceptional sales coach. You're passionate about helping people improve, naturally build trust with others, and know how to turn coaching moments into measurable performance gains.

You're someone who:

• Has successfully coached and developed B2C sales or contact center representatives.
• Is comfortable managing the training and development needs of 40+ sales representatives simultaneously.
• Loves being on the sales floor, listening to calls, identifying opportunities, and providing meaningful feedback.
• Holds people accountable while motivating them to perform at a higher level.
• Communicates with confidence, energy, and empathy.
• Takes initiative and is always looking for ways to improve training programs.
• Is organized enough to manage multiple priorities in a fast-paced environment.
• Embraces new technology and enjoys finding ways to make coaching more efficient.
• Has experience using AI tools such as ChatGPT or similar platforms to improve productivity, training content, or coaching effectiveness.
• Brings a growth mindset and enjoys continuously learning new skills.

Preferred Qualifications

• 2+ years of B2C sales training, sales enablement, or contact center coaching experience.
• Proven success improving sales performance through coaching and development.
• Experience facilitating classroom and virtual training sessions.
• Strong understanding of sales methodologies, objection handling, and consultative selling.
• Experience using QA platforms, call analytics, or AI-powered coaching tools is a plus.
• Familiarity with Learning Management Systems (LMS) and instructional design principles is preferred.

What We Offer:

• Competitive compensation with optimized health benefits (medical, vision and dental), 401K and FSA/HSA benefits
• Unlimited PTO
• Bonus opportunities based on performance
• Flexibility for a great work life balance
• Work building located in the heart of the city with beautiful views
• Comprehensive training and mentorship on an ongoing basis with career growth opportunities
• A friendly and diverse work environment with supportive colleagues and leadership team
• Professional autonomy

Bridge Legal is an equal opportunity employer and prohibits discrimination and harassment of any kind. We are committed to providing employment opportunities to all qualified applicants and employees without regard to race, color, religion, sex, national origin, age, disability, veteran status, or any other legally protected status as defined by applicable law. We welcome and encourage candidates from diverse backgrounds and experiences to apply for open positions.