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Proposal Analyst Remote Jobs in Chicago, IL (NOW HIRING)

micro1 AI

AI Data Trainer - MS Suite - Remote

Chicago, IL · Remote

$35 - $50/hr

... strategic proposals, or data-driven reporting, tailored to your industry background. * Document ... analyses. * Direct experience supporting or driving projects in strategy, operations, sales ...

micro1 AI

AI Data Trainer - MS Suite - Remote

Chicago, IL · Remote

$35 - $50/hr

... strategic proposals, or data-driven reporting, tailored to your industry background. * Document ... analyses. * Direct experience supporting or driving projects in strategy, operations, sales ...

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Proposal Analyst Remote information

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$24.7K

$78.6K

$141.6K

How much do proposal analyst remote jobs pay per year?

As of Aug 13, 2026, the average yearly pay for proposal analyst remote in Chicago, IL is $78,626.00, according to ZipRecruiter salary data. Most workers in this role earn between $69,000.00 and $87,600.00 per year, depending on experience, location, and employer.

What are some common challenges faced by remote proposal analysts, and how can they be effectively managed?

Remote Proposal Analysts often encounter challenges such as coordinating with dispersed teams across different time zones, maintaining clear communication, and accessing up-to-date information required for proposals. To manage these challenges, it's crucial to leverage collaborative tools (like Slack, Microsoft Teams, or shared document platforms), establish regular check-ins with your team, and set clear deadlines. Building strong relationships with subject matter experts and staying organized with a project management tool can also help ensure that all proposal components are accurate and submitted on time.

What does a proposal analyst do?

A Proposal Analyst working remotely is responsible for reviewing requests for proposals (RFPs), gathering relevant information, and creating compelling proposals to win new business for their organization. They coordinate with various departments—such as sales, finance, and technical teams—to ensure the proposal meets client requirements and aligns with company capabilities. Remote Proposal Analysts use digital tools to communicate, organize documents, and manage deadlines efficiently. Their work is crucial in helping companies secure contracts and grow revenue.

What are the key skills and qualifications needed to thrive as a proposal analyst?

To thrive as a Proposal Analyst (Remote), you need strong analytical skills, attention to detail, and a solid understanding of proposal writing, often supported by a bachelor's degree in business, communications, or a related field. Familiarity with proposal management software (like RFPIO or Qvidian), Microsoft Office Suite, and sometimes Shipley or APMP certification is typically required. Excellent written communication, time management, and collaboration skills help you effectively convey value propositions and work with cross-functional teams. These competencies are crucial for producing competitive, compliant proposals that win business in a deadline-driven, remote environment.

What are the most commonly searched types of Proposal Analyst jobs in Chicago, IL?

The most popular types of Proposal Analyst jobs in Chicago, IL are:

What are popular job titles related to Proposal Analyst Remote jobs in Chicago, IL?

For Proposal Analyst Remote jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Proposal Analyst Remote jobs in Chicago, IL look for?

The top searched job categories for Proposal Analyst Remote jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Proposal Analyst Remote jobs?

Cities near Chicago, IL with the most Proposal Analyst Remote job openings:

Proposal Analyst Remote jobs near you

Client Partner, SaaS Restaurant Sales (Remote - US)

Yelp, Inc

Chicago, IL • Remote

$55K - $65K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 23 days ago

Yelp rating

7.8

Company rating: 7.8 out of 10

Based on 8 frontline employees who took The Breakroom Quiz

136th of 244 rated software companies

Job description

Summary

Are you passionate about dining out and supporting local restaurants? Do you thrive in a fast-paced, sales-driven environment and love building meaningful relationships with clients? If so, we'd love to meet you.

Yelp's Guest Manager is a powerful front-of-house solution that helps restaurants create exceptional guest experiences and streamline their operations. With the largest restaurant discovery platform in the world behind it, Guest Manager helps restaurateurs attract more diners and deliver unforgettable hospitality.

As a Restaurant Client Partner, you'll take ownership of your pipeline and your success. You'll work with restaurants already using one or more Yelp products, helping them maximize value, expand their footprint, and connect more deeply with their communities. This is a full-cycle sales role, and we're looking for someone who thrives on the thrill of the close, bounces back quickly from setbacks, and thinks creatively to find solutions that drive real impact.

You'll also be part of the Yelp Sales Development Program, a structured growth track with clear expectations, performance milestones, and opportunities for advancement. We'll give you the training, tools, and support you need to succeed-but your grit, hustle, and hunger will take you the rest of the way.

We'd love to have you apply, even if you don't feel you meet every single requirement in this posting. At Yelp, we're looking for great people, not just those who simply check off all the boxes. This is a full-time remote role based in the United States.

What you'll do:
  • Own your book of business and sales pipeline from prospecting to close
  • Drive the full sales cycle through outbound outreach, discovery, solution selling, and negotiation
  • Identify upsell and cross-sell opportunities to expand current client relationships
  • Build lasting partnerships with restaurant owners, operators, and managers
  • Use creativity and persistence to overcome objections and tailor solutions
  • Consistently exceed monthly sales goals and performance metrics
  • Use Chatbench, Yelp's internal tool that provides secure access to a number of LLM models, to research, draft proposals, analyze data and overcome objections
What it takes to succeed:
  • Hold a Bachelor's degree and/or 1+ years of outbound sales experience
  • A go-getter mindset: you're scrappy, resilient, and motivated to succeed
  • Experience with restaurant technology (reservations, waitlist, or FOH systems) is a plus
  • Strong communication skills and high comfort level selling over the phone
  • A creative approach to problem-solving and value-based selling
  • Proven ability to prioritize, multitask, and stay organized in a fast-paced environment
  • Familiarity with Salesforce or similar CRM tools is a bonus
  • A team player mentality with a competitive edge
What you'll get:
  • Effective your first day: Full medical, vision, and dental 
  • 15 days PTO (accrual begins on date of hire and increases with 2+ years of tenure thereafter), 12 paid holidays, plus one floating holiday
  • Up to 14 weeks of parental leave
  • Monthly wellness subsidy
  • Work from home reimbursement
  • Flexible spending account
  • 401(k) retirement savings plan
  • Employee stock purchase plan
  • Compensation base salary is $55,000 - $65,000 annually + uncapped performance based incentives
  • For more information about US benefits at Yelp, please check out this link
ClosingAt Yelp, we believe that diversity is an expression of all the unique characteristics that make us human: race, age, sexual orientation, gender identity, religion, disability, and education - and those are just a few. We recognize that diverse backgrounds and perspectives strengthen our teams and our product. The foundation of our diversity efforts are closely tied to our core values, which include "Playing Well With Others" and "Authenticity." We're proud to be an equal opportunity employer and consider qualified applicants without regard to race, color, religion, sex, national origin, ancestry, age, genetic information, sexual orientation, gender identity, marital or family status, veteran status, medical condition or disability. Actual salary offered may vary based on multiple factors, including but not limited to, an individual's location and experience.  We will consider for employment qualified candidates with arrest and conviction records, consistent with applicable law (including, for example, the San Francisco Fair Chance Ordinance for roles based in San Francisco, the Los Angeles County Fair Chance Ordinance for roles based in the unincorporated areas of Los Angeles County, and the California Fair Chance Act for roles based in California). Where required by law, a criminal background check will not be conducted until after a conditional offer of employment is made, and any evaluation of a candidate's criminal background check will be subject to an individualized assessment that takes into account the candidate's specific criminal records and the responsibilities and requirements of the particular role. We are committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, you may contact us at accommodations-recruiting@yelp.com or 415-969-8488. Note: Yelp does not accept agency resumes. Please do not forward resumes to any recruiting alias or employee. Yelp is not responsible for any fees related to unsolicited resumes. US Recruiting and Applicant Privacy Notice Notice to Washington Applicants - Washington State Fair Chance Act #LI-Remote #CircaEmployment Type: FULL_TIME

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