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Remote Selling Jobs in Chicago, IL (NOW HIRING)

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... selling skills. • Self-discipline and consistency in a remote, commission-based environment. Preferred Qualifications • One or more years of life insurance, financial services, or inside sales ...

As a Client Executive, you'll be responsible for promoting our expert approach and selling our ... Remote Benefits & Equal Opportunity We value our employees and offer a comprehensive benefits ...

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... selling skills. • Self-discipline and consistency in a remote, commission-based environment. Preferred Qualifications • One or more years of life insurance, financial services, or inside sales ...

Be Seen First

... selling skills. • Self-discipline and consistency in a remote, commission-based environment. Preferred Qualifications • One or more years of life insurance, financial services, or inside sales ...

Are you sick of 'selling data' but love sales and want to do something more meaningful?Do you ... This role will be East Coast based-NY/NJ/CT or Chicago based, but will be remote. Please submit a ...

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Remote Selling information

See Chicago, IL salary details

$20.5K

$73.1K

$150.4K

How much do remote selling jobs pay per year?

As of May 28, 2026, the average yearly pay for remote selling in Chicago, IL is $73,072.00, according to ZipRecruiter salary data. Most workers in this role earn between $53,887.00 and $79,034.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Remote Sales Representative, and why are they important?

To thrive as a Remote Sales Representative, you need strong sales acumen, product knowledge, and a proven track record in meeting targets, often supported by a relevant degree or sales certifications. Familiarity with CRM platforms like Salesforce, video conferencing tools, and digital communication systems is essential. Exceptional communication, self-motivation, and relationship-building skills help you stand out in a remote environment. These abilities are vital for building trust, maintaining productivity, and achieving sales goals without in-person interaction.

What are some common challenges faced by professionals in remote selling, and how can they be overcome?

Remote selling professionals often face challenges such as building trust with clients without face-to-face interactions, managing time zones, and maintaining effective communication. To overcome these, it's important to leverage video calls and personalized messages to foster rapport, use digital tools to stay organized, and adapt communication styles to meet client preferences. Regular team check-ins and collaboration with marketing and customer support can also help address client needs promptly and ensure a seamless sales process.

What is remote selling?

Remote selling is the process of selling products or services to customers without meeting them in person, typically using digital communication tools like phone calls, video conferencing, email, or chat. This approach enables sales professionals to connect with prospects and clients from anywhere, increasing flexibility and efficiency. Remote selling has become increasingly popular due to advancements in technology and the rise of remote work, allowing businesses to expand their reach and reduce travel costs.

What is the difference between Remote Selling vs Inside Sales?

AspectRemote SellingInside Sales
CredentialsSales experience, communication skillsSales experience, communication skills
Work EnvironmentRemote, home-basedOffice or remote, depending on company
Industry UsageCommon in tech, SaaS, B2B salesWidely used across various industries
Job FocusEngaging prospects remotely, closing dealsEngaging prospects, managing sales pipeline

Remote Selling and Inside Sales both involve sales activities conducted remotely, often requiring similar skills and credentials. Remote Selling emphasizes closing deals independently from home, while Inside Sales may include a broader range of sales tasks, sometimes in a team setting. Both roles are vital in modern sales strategies and are frequently searched for by sales professionals seeking remote opportunities.

What are the most commonly searched types of Selling jobs in Chicago, IL? The most popular types of Selling jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Selling jobs? Cities near Chicago, IL with the most Remote Selling job openings:
Founding Account Executive - ~$350K OTE - Bay Area - AI Expert Services & Training Data - Remote US

Founding Account Executive - ~$350K OTE - Bay Area - AI Expert Services & Training Data - Remote US

RevsUp

Mundelein, IL • Remote

$350K/yr

Other

Medical, Retirement

Posted 26 days ago


Job description

Opportunity Overview – Founding AE, AI Expert Services (remote)


A growth-stage AI data company is hiring a Founding AE for its AI Expert Services vertical, a new revenue line selling subject-matter-expert (SME) services and human-generated training data into ~60–70 frontier AI labs and AI-native companies building foundation models (OpenAI, Anthropic, Google DeepMind, Meta, and peers). This is a quota-carrying, 0→1 individual contributor role for a builder who can create the GTM motion from scratch, land initial reference accounts, and expand a concentrated named-account territory into a repeatable $2M+ book of business.


A growth-stage AI data company is a ~100-employee, PE-backed AI data company recently acquired by a ~10,000-employee global platform. This role combines founder-level ownership with the infrastructure and scale of an established parent, operating within a highly concentrated TAM with only a handful of credible competitors. Fully remote in the US, W2 with full benefits, reporting to the SVP and Co-Founder.


Solution

The AI Expert Services vertical sells vetted, domain-expert human labor to frontier AI labs and AI-native builders. SMEs with deep fintech, healthcare, legal, and other regulated-industry expertise generate the post-training prompts, answers, reasoning traces, and evaluations that leading foundation models need to reach expert-level performance in high-stakes domains.


Unlike broad data-labeling vendors, AI Expert Services is a concentrated, high-margin offering: the company sources, vets, and manages credentialed SMEs (MDs, CPAs, JDs, PhDs, senior practitioners), then deploys them against model-training tasks billed on an hourly basis. The company’s existing platform, global operations footprint, and in-house contributor network of 500,000+ give this new vertical immediate scale advantages over the 6–7 competitors targeting the same TAM.

How the Business Works


AI Expert Services is an hourly, services-based business, not SaaS. Customers engage the company to stand up pods of credentialed SMEs against specific model-training workstreams, then expand scope as new domains, modalities, and evaluation needs emerge. Revenue is driven by landing initial projects, proving quality and throughput, and growing hours-per-account over time rather than by recurring subscriptions.


Role

• Founding, quota-carrying Individual Contributor reporting to the SVP and Co-Founder. Fully remote across the US with access to the San Francisco office. Travel required for key customer meetings, conferences, and strategic accounts.

• ~$350K OTE at a 40/60 base-to-variable split with a $2M quota. Uncapped comp designed to reward landing and expanding initial AI Expert Services accounts. W2 with full benefits including 401k and health plan. No equity due to PE-backed structure.

• Deal sizes range from $250K to $2M+ with meaningful expansion potential as SME pods scale. Hourly, services-based model where customers expand scope across domains and use cases. You own initial land and deep account expansion.

• First dedicated AE for the AI Expert Services vertical. You will build the GTM motion from scratch and own a concentrated territory of ~60–70 frontier AI labs and AI-native companies (OpenAI, Anthropic, Google DeepMind, Meta, etc.).

• Primary buyers include post-training leads, research engineers, heads of data, and AI product leaders. Pipeline is driven through targeted outbound, warm intros, and relationship-based selling into a tight buyer community. This is a consultative, technical sale where credibility matters.

• 8 to 10+ years of enterprise B2B sales experience closing $250K–$2M+ deals into AI-native or highly technical buyers. Direct experience selling expert services, RLHF, post-training data, or similar offerings is strongly preferred. Not a fit for SaaS-only or data-labeling-only backgrounds.

• Not for SMB or mid-market sellers, high-volume transactional reps, or candidates looking to learn AI.

• Priority hire. You will define the playbook, land initial reference logos, and build the foundation for the next wave of sellers.


Why Join

• Founding AE for a brand-new AI Expert Services vertical, defining the playbook end-to-end

• Founder-level ownership with the backing and infrastructure of a 10,000+ employee global platform

• Selling into the ~60–70 frontier AI labs building the world’s most important foundation models

• Uncapped comp (~$350K OTE, 40/60) with direct reporting line to the SVP and Co-Founder


Culture

• Acquired by a global services platform in February 2026, bringing the scale of a ~10,000-employee, PE-backed parent. The company operates independently with its own P&L and maintains a startup-oriented, agile culture.

• Co-Founder and hiring manager has 15+ years scaling startups in edtech and compliance.

• Rated 4.6/5 on Glassdoor (80 reviews, 92% recommend) and 4.3/5 on G2. Recognized with awards including Best AI Training Data Vendor (2023), Global AI Summit Award for Conversational AI, and Stevie Awards for Most Innovative Tech Startup.

• “The platform gave me access to top-tier pre-trained vision, NLP, and speech models with a simple, intuitive interface.” – G2 Review


Official Job Description


A growth-stage AI data company is hiring a Founding, quota-carrying Account Executive to launch and scale the AI Expert Services vertical across the US market. This is a 0→1 role owning pipeline development, the first reference accounts, and expansion of a concentrated named-account territory of ~60–70 frontier AI labs and AI-native builders. The Founding AE sells vetted subject-matter-expert (SME) services and human-generated training data on an hourly, services-based model into the teams building the world’s most important foundation models.


Key Responsibilities:

• Build the AI Expert Services GTM motion from scratch. Own the full enterprise sales lifecycle, from pipeline generation through close, across a named-account territory of ~60–70 frontier AI labs and AI-native companies building foundation models.

• Build trusted relationships with post-training leads, alignment teams, research engineers, and heads of data; translate customer model-training requirements (RLHF, evaluations, reasoning traces, domain expert prompts and answers) into structured SME pod engagements alongside internal solution and delivery teams. Land initial engagements, prove quality and throughput, and expand hours-per-account into seven-figure run rates.


Required Experience:

• 8–10+ years of enterprise B2B sales with a track record of closing $250K–$2M+ deals and demonstrated quota achievement at or above $2M. Comfort operating as a founding seller building a motion from scratch.

• Direct experience selling expert services, RLHF, post-training data, model evaluations, or adjacent AI model-training offerings into frontier AI labs or AI-native builders. Sellers from pure SaaS or data-labeling-only backgrounds will not be a fit.

Preferred Experience:

• Deep familiarity with frontier AI post-training workflows, RLHF pipelines, reasoning and evaluation data, and domain SME engagements (fintech, healthcare, legal, regulated industries). Experience selling into OpenAI, Anthropic, Google DeepMind, Meta, Mistral, or peer labs. Comfortable with globally distributed SME delivery teams.

• Tools: Salesforce, HubSpot, LinkedIn Sales Navigator, Apollo (or similar).


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About RevsUp

Sourced by ZipRecruiter

Industry

Recruiting and staffing services

Company size

51 - 200 Employees

Headquarters location

Scottsdale, AZ, US

Year founded

2015