Mapping Chicago's early-stage sales-tech venture landscape

Chicago is home to over 50 early-stage sales-tech ventures that have raised a combined $60M+ in venture capital. TechNexus maps the startups transforming how businesses drive growth, manage relationships, and optimize every stage of the sales process.

TechNexus continues its Reinventing Industry series with a spotlight on the Sales-tech sector in Chicago. A key hub for innovation, Chicago is home to over 50 early-stage Sales-tech ventures transforming how businesses drive growth, manage relationships, and optimize sales operations. Collectively, these companies have raised over $60 million in venture funding, illustrating the city’s strength in this rapidly evolving domain with applications across markets.

Sales strategies have undergone a seismic shift in the last decade. Traditional cold calls and in-person meetings have given way to digital engagement and data-driven decision-making. The rise of remote work and virtual selling has further accelerated the need for innovative solutions that streamline prospecting, personalize outreach, and optimize customer interactions. Companies now rely more on advanced analytics, automation, and AI tools to make smarter decisions, reduce inefficiencies in sales motions, and improve conversion rates.

Subcategories TechNexus is excited about:

Live Video Commerce: With companies like WhatNot (livestream marketplace) surpassing $2 billion in GMV in 2024 and TikTok making its foray into the live shopping space, it’s no secret that this new form of online shopping is seeing explosive growth. Consumers increasingly crave engaging, interactive, and authentic content-based shopping experiences - and platforms allowing brands/creators to build real-time connections with audiences are succeeding.

• Uptok ($900K Round): 1-on-1 video shopping consultations & customer service to conduct demos, close deals, and give customers a personalized buying experience
• Encore ($1.2M Round): Video commerce platform to buy and sell rare products and collectables via live auction

Digital Storefronts: 80% of consumers are more likely to make a purchase when brands offer personalized experiences. To capture growth in this space, companies are creating methods to revolutionize the way products, resources, and services are showcased and sold, enabling deeper consumer connections and boosting conversions.

• Showroom ($1.5M Round): AI powered, NLP search aggregator to create customized digital storefronts based on users brand preferences
• Kahana ($150K Round): Allows anyone to build tailored ‘hubs’ of digital products, resources, and files to share directly with prospective customers

Rewards Platforms: Brand loyalty, particularly with younger generations, is weakening. Since the pandemic, 57% of Gen Z shoppers are now less loyal to brands than before the pandemic. Customer engagement & rewards platforms are hoping to address this by improving the buying experience both in-person and online, ultimately enhancing brand loyalty for this new wave of consumers.

• Unplug ($1.5M Round): Restaurant ordering & engagement platform that offers loyalty discounts, omnichannel marketing, and a seamless ordering experience
• Bounty ($1.5M Round): Community-based rewards platform for members to browse and claim discounts/promos across brands

By Joey Alfieri at TechNexus Venture Collaborative