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Weekend Cold Calling Jobs in Milwaukee, WI (NOW HIRING)

TIMEPROOFUSA

Sales Representative

Milwaukee, WI

$150K - $320K/yr

Run pre-set, qualified appointments with homeowners--no cold calling or lead generation required ... Availability to work evenings and weekends. * Comfortable working in a commission-based role.

Sales and Marketing

Sales Representative

Milwaukee, WI · On-site

... cold calling; direct sales experience is preferred, but not required. Preferred Related Work ... weekends Variable hours: may include weekends, holidays, and split days off #LI-TS1 SMD311 2026 ...

SPECTRUM

Sales Representative

Milwaukee, WI · On-site

$30K/yr

... cold calling; direct sales experience is preferred, but not required. Preferred Related Work ... weekends Variable hours: may include weekends, holidays, and split days off #LI-TS1 SMD311 2026 ...

Winter Services

Branch Administrator

Kenosha, WI · On-site

$20 - $23/hr

Night and weekend hours * Update route books, customer scopes and maps * Load storm data and ... Appointment setting * Cold calling weekly in the summer * Call block day with sales team

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All JobsCold Calling JobsWeekend Cold Calling JobsWeekend Cold Calling Jobs in Milwaukee, WI

Weekend Cold Calling information

See Milwaukee, WI salary details

$16

$53

$90

How much do weekend cold calling jobs pay per hour?

As of Aug 6, 2026, the average hourly pay for weekend cold calling in Milwaukee, WI is $53.85, according to ZipRecruiter salary data. Most workers in this role earn between $34.57 and $76.25 per hour, depending on experience, location, and employer.

What are some typical challenges faced in a weekend cold calling role, and how can I overcome them?

Weekend Cold Calling professionals often encounter challenges such as reaching decision-makers outside standard business hours and handling a higher rate of unanswered calls. To overcome these, it's helpful to prepare engaging voicemail scripts, track optimal calling times for better response rates, and maintain a resilient, positive attitude. Regular feedback sessions with your team or supervisor can also help refine your approach and improve results over time.

What is weekend cold calling?

Weekend cold calling jobs involve reaching out to potential clients, customers, or leads by phone during the weekends, typically to promote products, services, or gather information. Employees in these roles follow a script or guidelines and often work from a call center or remotely. The goal is to generate interest, set appointments, or collect data, and these positions may require good communication and persuasion skills. Weekend hours are targeted to reach people who may not be available during the traditional workweek.

What is the difference between Weekend Cold Calling vs Weekend Telemarketer?

AspectWeekend Cold CallingWeekend Telemarketer
CredentialsHigh school diploma or equivalent; sales or communication skillsHigh school diploma or equivalent; sales or communication skills
Work EnvironmentOffice or remote; outbound sales callsOffice or remote; outbound sales or promotional calls
Industry UsageSales, telemarketing, customer acquisitionSales, telemarketing, promotional campaigns
Common Search IntentComparing roles involving cold calling on weekendsRoles focused on telemarketing during weekends

Weekend Cold Calling and Weekend Telemarketer roles both involve outbound calling to potential customers during weekends, often requiring similar skills and credentials. The main difference lies in the specific focus: cold calling emphasizes reaching out to new prospects, while telemarketing may include promoting products or services. Both roles are common in sales and telemarketing industries, with overlapping work environments and employer expectations.

What are the key skills and qualifications needed to thrive as a weekend cold caller?

To excel as a Weekend Cold Caller, you typically need strong verbal communication skills, a persuasive attitude, and prior experience or training in sales or telemarketing. Familiarity with customer relationship management (CRM) software and autodialing systems is often required. Resilience, persistence, and active listening are important soft skills that help build rapport and handle rejection effectively. These abilities are crucial for achieving sales targets, maintaining productivity, and creating positive customer interactions during high-volume calling periods.
What are the most commonly searched types of Cold Calling jobs in Milwaukee, WI? The most popular types of Cold Calling jobs in Milwaukee, WI are:
What are popular job titles related to Weekend Cold Calling jobs in Milwaukee, WI? For Weekend Cold Calling jobs in Milwaukee, WI, the most frequently searched job titles are:
What job categories do people searching Weekend Cold Calling jobs in Milwaukee, WI look for? The top searched job categories for Weekend Cold Calling jobs in Milwaukee, WI are:
Weekend Cold Calling jobs near you

Business Development Specialist

Drake & Associates

Waukesha, WI • On-site

Full-time

Posted 26 days ago

Job description

Drake & Associates is an independent financial planning firm dedicated to helping families retire with confidence and clarity. We are known for our integrity, education-first approach, and commitment to delivering an exceptional client experience.


Our culture is built on core values including Ultimate Client Experience, Extreme Ownership, Entrepreneurial Spirit, and Respect the Family. We believe in doing the right thing, supporting one another, and taking pride in the impact we make every day.


About This Opportunity

The Business Development Specialist will not rely on cold calling to convert leads; instead, you will engage leads after they have shown interest in one of our many marketing funnels, including informational workshop/seminars, webinars, radio ads, TV ads, social media, website leads, YouTube videos, paid social media, etc. The ideal candidate will be a good conversationalist, an excellent communicator, express a positive attitude, be persistent and confident. They will have excellent follow-up skills and can build relationships over phone, email and text, while never making the lead feel uncomfortable or pressured.


How You'll Make an Impact

  • Implement, and assist in the creation of, contact strategies to keep open leads engaged with the brand, including high-volume outbound calling to warm leads, appointment setting, confirmations, and event reminders, leveraging both phone and email
  • Leverage the brand’s content library, including TV and Radio show content, YouTube videos, podcast, editorial, webinar, whitepaper and the like to continue conversations with open leads that convey the long-term value that the brand can provide
  • Follow up with prospective clients during peak hours of availability and convenience, including nights and weekends when necessary
  • Assist in the management of the Advisor’s calendars through setting First Appointments relative to their availability and existing appointment schedule
  • Possess an awareness about upcoming events, content releases and other marketing strategies, and leverage these events to convert leads into appointments.


What We're Looking For

  • Bachelor’s degree preferred
  • Comfortable managing a high volume of outbound calls to warm leads while meeting daily activity targets
  • 2+ years’ experience working within a Financial Advisory firm, or within a Sales role tasked with scheduling appointments for a company
  • Excellent communication skills; both verbal and written
  • Proficient with Google Suite
  • Experience with Salesforce preferred, but not required


Key Traits

  • Highly personable with an optimistic outlook on work and life
  • Excellent communicator
  • Remarkable organizational and prioritization skills, with a meticulous attention to detail
  • Goal-driven team player with a result-driven approach
  • Superior aptitude in innovation and problem-solving PLUS meticulous attention to detail
  • Comfortable communicating over phone and in email, leveraging tools like Salesforce,
  • Google Suite, calendar scheduling, auto-dialers, SMS platforms and similar technology


Compensation Structure

This role provides a base salary along with a highly competitive commission structure that rewards strong performance, meaningful results, and contributions to our shared success.