Business Development Representative - Chicago

Waitwhile; Chicago (IL); On-site; USD 60,000 - 80,000; Full time

Benefits offered by this job

Health, dental, vision insurance

Unlimited PTO

401(k) with company match

HSA and FSA options

Life insurance

Tuition reimbursement

Wellness program

Job summary

Waitwhile, a growing SaaS company, seeks a Business Development Representative in Chicago. You will drive outbound prospecting to decision-makers, book qualified meetings, and build the pipeline for Account Executives.

You’ll shape how we prospect, test strategies, and contribute to early outbound practices. You’ll collaborate with Sales, Marketing, and RevOps, using tools like HubSpot, Amplemarket, and Trellus to keep data clean and drive results.

Qualifications

• 1–2+ years in B2B SaaS sales, business development, or outbound prospecting.
• Ability to work independently and take initiative.
• Comfort with building processes in a still-evolving outbound motion.
• Strong written and verbal communication skills, confident on the phone.
• Resilience, curiosity, and willingness to test and iterate quickly.
• Organized and detail-oriented with solid follow-through.
• High school diploma required; bachelor’s degree a plus.
• US work authorization; visa sponsorship not available.

Responsibilities

• Drive outbound prospecting to reach decision-makers and book qualified meetings for Account Executives.
• Research target accounts and tailor outreach to key stakeholders.
• Help shape outbound motion, messaging, cadences, and best practices.
• Manage prospecting tools and workflow to keep pipeline clean and prioritized.
• Ensure smooth handoffs to Account Executives for each opportunity.
• Collaborate with Sales, Marketing, and RevOps to share feedback and insights.

Skills

B2B SaaS sales

Self-starter

Independent work

Strong communication

Resilience

Organized

High school diploma

US work authorization

HubSpot familiarity

Amplemarket familiarity

Trellus familiarity

Startup experience

Mid-market/enterprise prospecting

Outbound messaging

Education

High school diploma

Bachelor’s degree preferred

Tools

HubSpot

Amplemarket

Trellus

Job description

Who we are

Here at Waitwhile we’re on a mission to eliminate the 1 trillion hours people spend waiting in lines every year. Our platform combines virtual waitlists, scheduling, real-time updates, messaging, and analytics to make access to places, services, and events seamless, online or in person. Trusted by 10,000+ companies, Waitwhile has already helped more than 250 million people enjoy a radically better waiting experience. Our clients include IKEA, Louis Vuitton, Costco, Delta Airlines and many more. We’re just getting started, and we need your help.

The role

We’re looking for a Business Development Representative to join our sales team, based in Chicago.

You’ll drive outbound prospecting to engage decision-makers, book qualified meetings, and build pipeline for our Account Executives. You’ll work closely with Sales, Marketing, and RevOps to improve targeting, messaging, and handoffs.

Our outbound motion is still taking shape, so this is not a role where you step into a finished machine. You’ll help shape how we prospect, test what works, and bring ideas that are heard and acted on.

This is a great opportunity for someone who wants to build, loves the energy of outbound sales, and is aiming for a career in closing deals.

What you’ll do

Drive outbound prospecting: Reach decision-makers in target accounts through cold calls, emails, LinkedIn, and other channels, and book qualified meetings for our Account Executives.

Research and personalize: Identify the right people within target accounts and tailor your outreach where it matters, while keeping strong activity levels.

Help build the outbound motion: Partner with sales leadership to refine targeting, messaging, and outreach strategy, and help set early best practices for outbound at Waitwhile.

Manage tools and workflow: Use Amplemarket, Trellus, ZoomInfo, and HubSpot to prospect, prioritize accounts, and execute outreach, and keep pipeline data clean and accurate.

Ensure great handoffs: Partner with our Account Executives to make sure every opportunity is aligned and every meeting starts on the right foot.

Collaborate cross-functionally: Share prospect feedback, market insights, and objections from your conversations with Sales, Marketing, and RevOps.

What skills you need

• 1–2+ years of experience in B2B SaaS sales, business development, or outbound prospecting, for example as a BDR or SDR.

• Strong self-starter mentality with the ability to work independently and take initiative.

• Comfortable operating in an environment where not everything is fully built yet.

• Strong written and verbal communication skills, and confidence on the phone.

• Resilience, curiosity, and a willingness to test, learn, and improve quickly.

• Organized and detail-oriented, with solid follow-through.

• A high school diploma (a bachelor’s degree is a plus).

• Legal authorization to work in the United States. We’re unable to offer visa sponsorship (e.g. H-1B, TN) for this position.
  Bonus Skills & Attributes:

• Familiarity with HubSpot, Amplemarket, Trellus, or similar prospecting tools.

• Founding, early-stage, or startup experience.

• Experience prospecting into mid-market or enterprise accounts.

• Experience selling to operations, CX, retail, healthcare, travel, or other service-heavy industries.

• Experience helping shape messaging, cadences, or outbound processes in a prior role.

A great place to work

We want Waitwhile to be an incredible place to work. We offer great benefits and perks, flexible working hours and lots of interesting challenges. We believe in making work rewarding, care about your development, and are committed to your success. For high performers, there is a clear path to an Account Executive role. Join Waitwhile at this exciting stage and help shape both our future and your own.

Backed by Allegion (NYSE: ALLE), a global leader in access management, Waitwhile combines the energy and opportunity of a growing SaaS company with the stability, resources, and benefits of a global organization. That includes health, dental and vision insurance, unlimited PTO, a 401(k) with a 6% company match and no vesting period, HSA and FSA options, company-paid short- and long-term disability, life insurance, tuition reimbursement, and a wellness program with up to $2,000 in rewards.

Compensation: Base salary of $60,000–$80,000, with an OTE of $85,000–$115,000. Actual compensation is based on skills, experience, and other factors permitted by law.

Waitwhile has a positive, diverse, and supportive culture. We look for people who are curious, inventive, and work to be a little better every single day. We aim to be smart, humble, hardworking and, above all, collaborative. If this sounds like a good fit for you.