As the home to over 20 unicorns and some of the largest enterprises in the world (like Google, Microsoft, IBM, and Salesforce), Chicago’s tech industry has grown 18% in the last decade, creating an unprecedented need for knowledgeable and well-connected sales recruiting agencies. Whether your company is looking for its first AE or a seasoned sales executive, your recruiting agency should be knowledgeable about your business’ unique needs and prepared to address them.
Below are the top 10 sales recruiting agencies in Chicago, highlighting their areas of expertise, services, and unique approaches to help you decide which firm aligns best with your talent acquisition goals.
1. Betts Recruiting
Founded in 2009, Betts Recruiting is the national leader in go-to-market (GTM) hiring for sales, marketing, ops, and customer success roles for high-growth tech companies. With a deeply vetted talent network of sales professionals and its own proprietary technologies, Betts Recruiting has helped over 10,000 early- and growth-stage companies scale, including 75 unicorns reaching IPO. The firm’s specialized industry focus makes it the top trusted recruiting agency in the Windy City.
Betts’ innovative recruitment technology offers your company a diversity of hiring solutions to meet your specific needs. On Betts Connect, a self-service hiring platform, your company can access vetted GTM professionals, including their detailed Key Performance Indicators. This resource allows your hiring team to control candidate sourcing, while Betts’ RaaS offers a hybrid recruiting model. This subscription service offers direct, high-touch support from a Betts recruiter.
Betts recruiters bring a strategic, consultative approach to the hiring process, developing a deep understanding of your company’s culture to connect you with aligned, revenue-generating candidates. To gain access to valuable industry expertise and compensation insights, your company can utilize the firm’s free-to-use intelligence platform, Comp Engine.
2. Bespoke Partners
Founded in 2011, Bespoke Partners recruits executive-level GTM roles for technology and SaaS companies. From C-Suite to departmental positions, such as Chief Revenue Officers, VP of Sales, Chief Sales Officers, and other cross-functional roles like CEOs and CFOs, this firm’s focused recruitment services and proprietary hiring platform make it a trusted partner when hiring leadership roles.
Recruiters are capped at six searches at a time, ensuring intensive focus on your company’s needs as well as a timely hiring process. The firm emphasizes its high level of reliability with a one-year placement guarantee.
By partnering with Bespoke Partners, your company also has access to Calibrator, the firm’s proprietary hiring platform. Functioning like an AI-powered search engine, this resource helps your company find executive-level candidates that match with your preferences.
3. Sales Talent, Inc
Founded in 1999, Sales Talent, Inc specializes in GTM recruiting for scaling venture- and private equity-backed companies in North America. With niche expertise in the SaaS, AI, and FinTech industries, this firm understands the unique sales needs of Chicago’s most innovative organizations.
Recruiters at Sales Talent, Inc dedicate an average of 62 hours to each search, compared to the industry standard of 23 hours. This intensive headhunting approach helps recruiters hire most candidates in just over a week. Sales Talent, Inc values culture fit and interviews each candidate twice to ensure that your new hire aligns with your company’s values.
4. Talentfoot
Talentfoot is a boutique, Chicago-based firm that hires mid- to senior-level roles in a variety of functions, including Sales and Marketing. With deep local expertise and a specialized focus in scaling, Talentfoot has been a trusted partner for start-ups, scale-ups, and mid-market businesses hoping to achieve record revenue growth since 2010.
Led by its dedication to accelerating clients’ growth, Talentfoot implements a consultative approach to place candidates within seven days on average. Potential hires are discovered through a combination of behavior assessments, quota-based vetting, well-established Chicago connections, and a talent network of over 100,000 SaaS sales leaders. The firm also offers retained search services, like strategic talent mapping and performance metrics analysis.
5. HireWell
Founded in 2001, HireWell is a global, Chicago-based recruitment firm that partners with businesses in a diversity of industries, including SaaS, manufacturing, real estate, healthcare, and others. The firm combines consultative insights and proprietary recruitment technology to hire for GTM, Technology, Corp, and Industrial functions.
HireWell adopts a “culture-add” over “culture-fit” mindset, seeking candidates that will add value to your team. To streamline initial candidate sourcing, the firm leverages its recruitment technology, Rainmakers. This platform, a self-serve talent marketplace, gives your company access to a network of 350,000 specialized sales professionals, including a curated group of candidates.
6. Aldebaran Recruiting
Founded in 2001, Aldebaran Recruiting places marketing, advertising, public relations, and sales candidates across the SaaS, e-commerce, retail, and life sciences industries. Its Chicago presence makes it a valuable partner for businesses hoping to tap into local talent networks or better understand the city’s market dynamics.
With an emphasis on quality over quantity, Aldebaran Recruiting presents only 5-10 targeted resumes for each role, saving your company significant time and energy. The firm adopts a consultative approach to understand your company’s ideal hire and provides insights regarding candidate engagement throughout the hiring process.
7. Captivate Talent
Captivate Talent recruits GTM, Executive, and RevOps roles exclusively for early- to growth-stage SaaS startups. Since 2017, the firm has offered valuable connections across the industry, making it a valuable resource for many Chicago-based startups.
This firm’s recruiting process begins with a strategy call to understand your company’s needs and followed by thorough candidate screenings. To ensure longterm success, Captivate Talent offers valuable insights regarding hiring locations, compensation strategies, and brand leverage throughout your partnership.
8. Blueprint Expansion
Blueprint Expansion’s highly boutique recruitment services include sourcing remote GTM talent for SaaS companies. Since 2019 the firm has worked with organizations of all sizes, from startups to publicly traded companies, operating on the belief that remote work and regional expansion leads to revenue growth.
This firm implements scalable hiring practices that can be applied across industries and for companies at various stages of growth. With its consultative, headhunting approach, Blueprint Expansion actively looks for overlooked candidates beyond tech hubs. For high-growth SaaS companies in Chicago open to expansion or a remote workforce, Blueprint Expansion is an ideal partner to consider.
9. Insight Global
As one of the largest global professional services and staffing firms in the world, Insight Global employs over 3,000 full-time recruiters and places over 50,000 candidates each year across dozens of different industries. The firm partners with organizations of all sizes, from startups to large enterprises, and has partnered with over 800 Fortune 1000 companies, making it a trusted partner for many of Chicago’s most competitive businesses.
With a global talent network of over 5.2 million pre-screened candidates from more than 50 countries and over 24 years of sales recruiting experience, Insight Global adopts an aggressive headhunting approach to target candidates working for your company’s competitors.
10. Korn Ferry
As a global consulting and recruiting firm, Korn Ferry’s team of behavioral scientists, economists, and business leaders help organizations find solutions to their growth and hiring challenges. This firm’s team of specialized sales and tech recruiters sources candidates at all levels of seniority in the food service, medical devices, pharmaceuticals, real estate, and software industries.
Korn Ferry’s recruitment philosophy emphasizes candidate personality, believing that traits like curiosity, passion, and drive are stronger indicators of competence than previous sales experience. Recruiters utilize assessments Success Profiles, which are benchmarks that define the characteristics required for high performance in various positions. Korn Ferry also offers sales effectiveness consulting services, providing your company with valuable insights and expertise to build a successful sales team.
SDR SALARY EXPECTATIONS IN CHICAGO FOR 2025
SDR (Entry-Level)
Base + OTE: $55K–$70K | $70K–$85K
SDR (6+ Months Experience)
Base + OTE: $60K–$75K | $80K–$100K
2025 TRENDS SHAPING SDR HIRING IN CHICAGO
The rise of AI is uniquely impacting various sales functions as processes become more streamlined, entry-level roles are eliminated, and new products are introduced to the market. In Chicago, where AI is a leading industry, there is a growing demand for various roles and skills to help companies stay competitive.
Many technology companies are seeing a need for knowledgeable sales engineers who can understand and explain the technology behind new AI products and services, as well as the business value of purchasing them.
In lieu of cold outreach approaches, relationship building-skills are also becoming more valuable. This is especially true in roles like Account Executives (AEs), who are now expected to manage full sales cycles as entry-level roles are eliminated. As tech companies target larger companies with longer, more complex sales cycles, they are also seeking personable Enterprise Sales Development Representatives, who can foster trust with new and existing clients.
Contact Betts Recruiting to access Chicago’s top sales talent and navigate today’s unique GTM demands. We remain the leading employment agency in Chicago and bring years of seasoned expertise to the city’s increasingly competitive market.