Best Outbound Sales Agencies in Chicago

Looking for a partner to scale outbound prospecting, fill your sales pipeline, and book more qualified meetings? Below are the best Chicago B2B outbound sales agencies that specialize in outbound sales, appointment setting, and lead generation.

Hugo

Hugo is a Chicago-headquartered sales-support and outsourced SDR agency that builds outbound sales programs and will act as an extension of your sales team. They provide list building, intent data, cold outreach (phone + email + LinkedIn), appointment setting and full pipeline operations so your closers receive qualified leads and booked discovery calls. Hugo emphasizes integration with your CRM, actionable reporting on top outbound sales metrics, and predictable pipeline generation while helping manage customer acquisition cost and lead quality.

Highlights:

• Services: B2B lead generation, appointment setting, cold calling and email outreach.
• Focus on pipeline ops: CRM updates, quota tracking and weekly reporting.
• Uses intent data and market research to prioritize potential customers.
• Built to reduce CAC and produce predictable pipeline for sales reps.
• Rapid onboarding and SLA-driven outbound sales activities.

Check them out: https://hugoinc.com/

TelePro Group

TelePro Group runs managed inside-sales and outbound campaigns from Chicago offices. Their services include temporary & managed SDR staffing, appointment setting, B2B cold calling and list scrubbing. TelePro positions itself as a partner for companies needing on-demand outbound sales reps and running multi-channel outreach (phone calls + email outreach) to contact prospects, reach decision makers, and convert outbound leads into qualified meetings.

Highlights:

• Offers managed outbound campaigns and onsite temporary SDR staffing.
• Strong experience with appointment setting and multi-step outreach.
• Cleans and enriches contact data to improve contact rates.
• Helps accelerate the sales process and hand off qualified leads.
• Useful when you need flexible SDR capacity or short ramp pilots.

Check them out: https://teleprogroup.com/

LevelUp Leads

LevelUp Leads is an outsourced SDR and appointment-setting agency that runs cold calling, email outreach and LinkedIn prospecting to build an outbound sales pipeline. They provide fractional SDRs, full-service SDR programs, and cold-calling teams that focus on qualifying prospects, securing meetings with decision makers and delivering measurable outbound sales metrics for your sales team. Their offering centers on generating high quality leads and predictable pipeline for closers.

Highlights:

• End-to-end SDR services: list building, outreach, qualification, appointment setting.
• Cold calling and cold email + LinkedIn sequencing for outbound prospecting.
• Emphasis on measurable outbound sales metrics and conversion reporting.
• Fractional SDRs and scalable teams to control customer acquisition cost.
• Integrates with your sales process and CRM for smooth handoffs.

Check them out: https://levelupleads.io/

Rise25

Rise25 helps B2B firms drive warm outbound introductions and appointment setting using content-driven outreach and relationship programs (podcast-based ABM, outreach sequences and follow-up). For companies that need a personal, multi-channel outbound sales strategy to reach decision makers, Rise25 blends content marketing with outbound prospecting to create higher-quality conversations and qualified leads.

Highlights:

• Combines content (podcasting/ABM) with outbound prospecting to contact prospects.
• Focus on getting in front of decision makers and generating qualified leads.
• Appointment setting and warm outreach to prospects in target market.
• Useful for account-based outbound sales strategies and high-intent outreach.
• Personal touch and multi-channel cadence (email + phone + content).

Check them out: https://rise25.com/

Windy City Call Center

Windy City Call Center is a Chicago-area call center that provides B2B outbound calling, lead generation and appointment-setting programs. They specialize in high-volume outbound sales calls, scripted qualification, and handoffs to internal sales teams - a practical choice if your outbound sales strategy includes phone-first outreach and you need predictable outbound sales activities at scale.

Highlights:

• Phone-first outbound campaigns and large dialing capacity.
• Appointment setting, list follow-up and lead qualification.
• Keeps contact data and CRM updates for pipeline hygiene.
• Good for companies looking to scale cold calling and outbound calls.
• Focus on measurable outbound sales metrics (connect rates, booked meetings).

Check them out: https://www.windycitycallcenter.com/

Tele Business USA

Tele Business USA offers call center and outbound sales services from the Chicago suburbs with a focus on appointment setting, B2B lead generation, and list management. They run multi-step outbound sales processes (initial contact via phone or email, follow-ups, and appointment scheduling) to generate qualified leads for sales reps and reduce time to first meeting.

Highlights:

• Services: outbound leads, appointment setting, tele-prospecting.
• Helps lower CAC by delivering pre-qualified prospects to closers.
• Integrates phone calls and email outreach for multi-channel contact.
• Useful for ongoing outbound sales efforts and short pilot campaigns.
• Maintains reporting on top outbound sales metrics and conversion.

Check them out: https://www.tbiz.com/

Scale Virtually

Scale Virtually is a Chicago-area B2B lead generation and appointment-setting firm that supplies outsourced SDRs and remote sales support. Their offerings include cold calling, email outreach, lead qualification, and CRM operations so your sales team can focus on closing deals while the agency runs outbound prospecting and schedules discovery calls.

Highlights:

• Fractional/outsourced SDR teams and appointment setting.
• Focus on list building, contact data and outreach optimization.
• Tracks outbound sales metrics and pipeline velocity.
• Good for startups/small businesses needing predictable pipeline.
• Integrates with client sales processes to hand off qualified leads.

Check them out: https://scalevirtually.com/

Salesforge - An Alternative Approach To Outbound Sales

Instead of going through the hassle of dealing with an agency, why not seamlessly streamline a grand majority of the process for a fraction of the cost?

Salesforge is a cold outreach tool built for not just more outbound sales activity but more closed deals and a predictable pipeline as well.

Salesforge's highlights include:

• Multi-channel outreach (email + LinkedIn sender infrastructure).
• Warmforge - proprietary premium deliverability suite.
• Multi-mailbox / sender management (unlimited mailboxes, unlimited LinkedIn senders, unlimited shared workspaces & unlimited seats).
• Chrome extension + mobile app availability.
• Automatic AI email and LinkedIn message generation.
• Multi-source AI hyper-personalization capabilities.
• Spam / email-content checker and blacklist/IP health tools.
• Extensive integrations & campaign analytics.
• Transparent pricing.
• An optional AI SDR (Agent Frank) for prospecting and meeting booking.
• Robust documentation & responsive support.

All agencies above can run effective outbound sales activities, but if your top priority is a plug-and-play outreach tool with multi-source hyper-personalization, premium deliverability, and campaigns optimized to the fullest potential - Salesforge is the better alternative.

Try the 14 day free trial today

Or in case you still haven’t found the right option for your business, feel free to take a look at our certified Forge Experts!

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