6 Best Outplacement Services Firms in Chicago for Sales Professionals

More than 1.2 million jobs were cut in 2025, with layoffs hitting roles across tech, retail, and finance. Sales haven’t been spared either, with many companies scaling back revenue teams.

Getting laid off from a sales role hits differently. Your income depends on performance, your network drives opportunities, and your track record of deals and quotas doesn’t always translate cleanly onto a resume.

In a city like Chicago, where sales roles span tech, finance, healthcare, and manufacturing, there’s no shortage of outplacement firms. But most are built for general roles, not revenue-driven careers. That often leads to generic coaching that misses how sales professionals actually get hired.

Outplacement services typically range from $500 to $10,000 per employee, averaging around $1,900. But that number hides a big gap in quality.

For sales professionals, the difference comes down to this: can they help you position your revenue impact, negotiate compensation properly, and connect you with the right hiring managers?

This guide breaks down the six best outplacement firms for sales professionals in Chicago based on real outcomes.

Outplacement Services Firms in Chicago for Sales Professionals: At a Glance

1. WeAreCareer — Best Overall for Sales & GTM Professionals

WeAreCareer is an outplacement and reverse recruiting firm that actively manages the job search instead of just offering coaching. Instead of providing resources and leaving candidates to apply on their own, a dedicated team handles applications, recruiter outreach, and pipeline management.

This approach fits sales professionals well, especially at the manager, director, VP, and tech sales or GTM level, where consistent outreach and follow-ups drive results.

WeAreCareer has supported 1,200+ outplacement candidates and over 3,000 professionals overall, with structured coaching, ongoing support, and clear progress tracking for employers.

Key Features:

• Full job search execution (applications, recruiter outreach, interview booking)
• Dedicated career coach + career agent team
• Resume and LinkedIn profile full revamp
• Minimum interview guarantees on select programs
• Lifetime access to Career Course and resource library
• Real-time communication via built-in messaging platform
• Transparent per-employee pricing for companies
• Progress reports for HR teams

WeAreCareer Pricing

• Bronze: $1,500 (Analyst, Associate, Engineer)
• Silver: $2,700 (Manager, Team lead, Senior IC)
• Gold: $3,900 (HoD, Director, VP, C-suite)

WeAreCareer Review

Review: The team helped me rethink my targeting strategy and update my resume so it better matched the roles I was aiming for.

2. Challenger, Gray & Christmas

Challenger, Gray & Christmas is a Chicago-based outplacement firm and one of the oldest in the US, founded in 1966. Its long history in Chicago gives it strong local market knowledge and deep ties to the business community.

The firm offers outplacement and executive coaching across all levels, including sales roles, with a focus on industry-specific guidance and faster transitions. Programs include personalized coaching, targeted job matching, and access to a data-driven platform with job leads, career assessments, and performance tracking.

Reported results include an average 2.7-month placement time, with 96% of candidates landing equal or better roles and a 97% recommendation rate.

Clients typically work one-on-one with a dedicated coach, supported by structured guidance on resumes, job search strategy, and networking.

Key Features

• Chicago-based headquarters with 60+ years of local market expertise
• AI-powered CareerSuite platform with job matching and career assessments
• One-on-one coaching with full-time dedicated coaches
• Executive coaching practice alongside outplacement
• Quarterly performance reporting for employers
• Global reach through Career Star Group partnership

Challenger, Gray & Christmas Pricing

Pricing is not publicly listed, it’s customized per company and employee level.

Challenger, Gray & Christmas Review

Review: Great company full of caring individuals. True job search experts! Each individual who works there truly goes out of their way to help.

3. LHH (Lee Hecht Harrison)

LHH is a global outplacement and talent solutions firm with over 12,000 professionals across 60+ countries and more than 50 years of experience. Backed by The Adecco Group, it operates at large scale, supporting hundreds of thousands of career transitions each year.

For sales professionals, LHH focuses on personalized coaching and structured support. Each candidate works with a certified coach, supported by the Career Studio platform, which includes real-time market data, AI-driven insights, and guided tools throughout the job search.

A key strength is personal branding. LHH helps build resumes, LinkedIn profiles, and positioning strategies, and distributes over 150,000 candidate profiles monthly to hiring teams, increasing visibility in the market.

Programs include ongoing placement support until landing, with flexible timelines based on employee needs. LHH also offers reskilling through partnerships with General Assembly and LinkedIn Learning, helping candidates move into new roles or industries more effectively.

Key Features

• Global reach with local Chicago delivery
• AI-powered LHH Career Studio with real-time market data
• Certified career coaches with empathy-driven approach
• Personal branding package (resume, LinkedIn, and more)
• Access to General Assembly and LinkedIn Learning for upskilling
• Active placement support until landing

LHH Pricing

• Starts at ~$2,400 per employee for basic programs
• Mid-level programs: $5,200 – $10,000 depending on duration
• Executive / high-touch: $11,000+ per employee

LHH Review

Review: Thanks to Heather I was offered my first new role for 15 years (after 28 years with the same company) and I am very much looking forward to my new career.

4. INTOO

INTOO is a global outplacement provider with over 20 years of experience, operating in 130+ countries and delivering career transition support in Chicago and beyond.

The key differentiator is on-demand coaching. Candidates get instant access to career coaches 7 days a week, with no scheduling, no delays, and no limits on usage.

For sales professionals, this is especially valuable. The job search can be unpredictable, and having immediate support for interviews, follow-ups, and decision-making mirrors the kind of responsiveness expected in sales roles.

INTOO supports faster transitions, with claims of helping candidates move up to 2.5x faster, offering resume help, interview prep, and networking support throughout.

Programs are flexible and can be launched quickly, sometimes within hours, and are backed by Gi Group, a global HR and talent solutions provider.

Key Features

• Unlimited on-demand coaching, 7 days a week (no appointments needed)
• Service activation within 2 hours to 2 days
• Whole-human coaching approach (professional and personal well-being)
• Upskilling and reskilling courses included
• Employer dashboard for tracking progress
• Global reach across 130+ countries

INTOO Pricing

Pricing is custom and not publicly listed. It depends on level, duration, and scope.

INTOO Review

Review: I use INTOO for our company's outplacement services, and we've had a really good experience with the executive that we put through the program.

5. Careerminds

Careerminds is a global outplacement provider known for its tech-enabled, fully virtual model and personalized coaching. The company combines one-on-one career support with a digital platform designed to help employees transition faster and at a lower cost than traditional firms.

A key differentiator is flexibility. Instead of rigid programs, Careerminds offers customized outplacement plans with unlimited coaching access in some tiers and support that continues until the candidate lands a new role.

For sales professionals, this model works well. The combination of coaching, structured job search strategy, and continuous support mirrors a pipeline-driven approach, while the virtual setup allows access from anywhere without being tied to a physical office.

Careerminds also positions itself as a more cost-efficient alternative to traditional firms, with claims of up to 70% savings compared to legacy outplacement providers.

Key Features

• Fully virtual, tech-enabled outplacement model
• Personalized one-on-one coaching
• Support until job placement in many programs
• Global delivery across multiple markets and languages
• Lower-cost structure compared to traditional firms

Careerminds Pricing

Pricing is not publicly fixed and is fully customized

Careerminds Review

Review: Erica was a great help to me during an unplanned transition from one job to another.

6. Ascend Career and Life Strategies

Ascend Career and Life Strategies is a nationwide outplacement provider known for its highly personalized approach, offering tailored support for each employee and organization. Its office at 401 North Michigan Avenue gives it a strong in-person presence in Chicago.

For sales professionals who prefer face-to-face interaction, this physical presence is a clear advantage. Programs include a dedicated career coach, regular coaching sessions (in-person or virtual), resume and LinkedIn support, and a structured Career Marketing Action Plan.

Ascend also goes further than most firms by offering spousal career support, access to financial guidance, and assistance during the termination process itself.

A key differentiator is ongoing support, even after the formal program ends; continued guidance remains available, backed by a 100% satisfaction guarantee.

Key Features

• Physical office on Chicago's Magnificent Mile for in-person coaching
• Individualized Career Marketing Action Plan for every client
• Full resume, cover letter, LinkedIn, and social media support
• Spousal/partner career coaching included at no extra charge
• Staffing agency and recruiter network connections
• 100% Client Satisfaction Guarantee
• Post-engagement support included

Ascend Career Pricing

Pricing is not publicly fixed and is fully customized based on program scope and employee level.

Ascend Career Review

Review: Very good teaching skills with all practical examples, and helped me a lot in getting job. I recommend Ascend Career for online education.

The Bottom Line: WeAreCareer is the Best Outplacement Service in Chicago for Sales Professionals

Getting laid off from a sales role in Chicago requires more than generic outplacement support. The right partner directly impacts how quickly and effectively the next role is secured.

WeAreCareer stands out for sales professionals because the model is built around execution. The approach aligns with how sales work, focusing on pipeline, outreach, and consistent follow-ups. Instead of only offering coaching, the job search is actively managed through applications and recruiter outreach, with support continuing until placement.

For companies, this leads to stronger outcomes for departing employees. For candidates, it means having a team running the search rather than handling everything alone.

Visit WeAreCareer now to schedule a consultation and learn how the outplacement program works!