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Remote First Jobs in Chicago, IL (NOW HIRING)

Novum Global

Senior Account Executive

Chicago, IL · On-site +1

What We Offer - Remote-first flexibility and work-life balance. - Competitive base salary + uncapped commissions. - Health, dental, and vision benefits. - Opportunity to work with top-tier legal ...

Cribl

Customer Success Engineer, Chicago

Chicago, IL · On-site +1

With a global workforce, we're remote-first and grounded in a simple idea: software is a people business. Cribl is the place where curious, collaborative people can do their best work, grow fast, and ...

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Remote First information

What is the difference between Remote First vs Remote Customer Support Specialist?

AspectRemote First
Work EnvironmentCompany prioritizes remote work for all employees, with flexible policies and minimal in-office requirements.
Required CredentialsTypically requires relevant experience in remote work settings, communication skills, and industry-specific knowledge.
Employer & Industry UsageCommon in tech, marketing, and customer service sectors emphasizing flexible work models.

Remote First companies fully embrace remote work as the standard, whereas Remote Customer Support Specialists are specific roles within such companies, focusing on customer interactions remotely. The main difference lies in company policy versus role function, with Remote First indicating company-wide remote policies and Remote Customer Support Specialist referring to a job position within that framework.

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

To thrive in a Remote First role, you need strong self-management, digital communication, and time management skills, often supported by prior remote work experience and proficiency in collaborative platforms. Familiarity with tools like Slack, Zoom, project management software, and secure remote access systems is crucial. Proactive communication, adaptability, and self-motivation are standout soft skills for remote environments. These abilities ensure productivity, collaboration, and accountability without direct in-person supervision.

What are the main challenges and benefits of working in a remote-first company environment?

Working in a remote-first company offers flexibility and the opportunity to collaborate with a diverse team from various locations, but it also presents unique challenges. Remote employees often need to be proactive communicators and manage their own schedules to stay productive, as daily interactions can be less spontaneous than in a traditional office. Building strong relationships and maintaining team cohesion requires intentional effort through digital tools and regular virtual meetings. However, remote-first environments typically provide autonomy, support for work-life balance, and access to roles regardless of geographic location, making them appealing for many professionals.

What does 'Remote First' mean in the context of jobs?

'Remote First' refers to a work policy or company culture where working remotely is the default mode of operation. Employees are encouraged or expected to work from locations outside of a traditional office, and company systems, communication, and workflows are designed to support remote work. While some in-person workspaces may be available, they are typically optional or secondary. This approach allows for greater flexibility, access to a broader talent pool, and often improved work-life balance for employees.
What are the most commonly searched types of First jobs in Chicago, IL? The most popular types of First jobs in Chicago, IL are:
What are popular job titles related to Remote First jobs in Chicago, IL? For Remote First jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote First jobs in Chicago, IL look for? The top searched job categories for Remote First jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote First jobs? Cities near Chicago, IL with the most Remote First job openings:
Remote First jobs near you

Senior Account Executive

Novum Global

Chicago, IL • On-site, Remote

Full-time

Medical, Dental, Vision

Posted 23 days ago

Job description

The Role

As a Senior Account Executive, you will be responsible for identifying, developing, and closing new business opportunities, as well as expanding existing client relationships. You’ll work closely with senior stakeholders in Enterprise law firms to understand their operational and technology challenges and propose tailored solutions powered by our services and strategic technology partners.

Key Responsibilities

- Drive new business through outbound prospecting, networking, and lead follow-up.

- Manage the full sales cycle — from discovery and demo through to proposal, negotiation, and close.

- Cultivate strong relationships with partners, IT directors, COOs, and other law firm decision-makers.

- Sell a broad portfolio of solutions and services including document management systems, practice management, consulting, and integrations.

- Collaborate with technical consultants and project managers to scope solutions and ensure a smooth handoff post-sale.

- Stay current on legal tech trends, competitive landscape, and partner offerings.

- Consistently meet or exceed revenue targets and pipeline goals.

    Requirements

    - 5+ years of B2B sales experience, preferably in legal technologu or professional services.

    - Proven track record of closing complex deals with large law firms.

    - Strong understanding of law firm operations, workflows, and challenges.

    - Experience with enterprise systems like iManage, NetDocuments or Intapp is highly desirable.

    - Excellent communication, presentation, and negotiation skills.

    - Self-starter with the ability to manage multiple priorities and work independently in a remote environment.

    - CRM proficiency (e.g., Salesforce, HubSpot) for tracking pipeline and activity.

      What We Offer

      - Remote-first flexibility and work-life balance.

      - Competitive base salary + uncapped commissions.

      - Health, dental, and vision benefits.

      - Opportunity to work with top-tier legal clients and technologies.

      - Supportive, collaborative, and entrepreneurial culture.