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50 Wintrust Financial Human Resources Manager Jobs Hiring Near You

Wintrust

VP, Business Strategy - WLF

Rosemont, IL · On-site

$98K - $132K/yr

... managers to ensure internal resources are collaborative and projects/work streams are on time and in line with expectations * Partner with WLFs Strategic Initiative Owners, Wintrust's ePMO and ...

Wintrust

A/P Representative

Rosemont, IL

Wintrust provides community and commercial banking, specialty finance and wealth management ... Knowledge of Workday ERP or other similar ERP systems highly desirable. Benefits Medical Insurance ...

Wintrust

Senior Data Engineer

Rosemont, IL · Hybrid

$160K/yr

Wintrust provides community and commercial banking, specialty finance and wealth management ... Serve as a resource to internal and third-party team members on escalated issues and analyze and ...

Wintrust

Senior Data Engineer

Rosemont, IL · On-site

$160K/yr

Wintrust provides community and commercial banking, specialty finance and wealth management ... Serve as a resource to internal and third-party team members on escalated issues and analyze and ...

Wintrust

Senior Cloud Solutions Architect

Rosemont, IL · On-site

$64 - $87.75/hr

Wintrust provides community and commercial banking, specialty finance and wealth management ... Establish guardrails for resource provisioning to ensure security compliance (HIPAA, GDPR, SOC2 ...

Wintrust

Principal Data Architect

Rosemont, IL · On-site

Wintrust provides community and commercial banking, specialty finance and wealth management ... Serves as resource to internal, offshore team & third-party team members on escalated issues ...

Wintrust

Senior Cloud Solutions Architect

Rosemont, IL

$64 - $87.75/hr

Wintrust provides community and commercial banking, specialty finance and wealth management ... Establish guardrails for resource provisioning to ensure security compliance (HIPAA, GDPR, SOC2 ...

Wintrust

Principal Data Architect

Rosemont, IL · On-site +1

Wintrust provides community and commercial banking, specialty finance and wealth management ... Serves as resource to internal, offshore team & third-party team members on escalated issues ...

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Wintrust Jobs Information

Do workers at Wintrust get paid breaks?

No. Most people don’t get paid breaks.
68% of people say they don’t get paid breaks.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Does Wintrust pay people when they’re sick?

Yes. Most people get paid when they’re sick.
90% of people say they would get paid if they were sick but scheduled to work.
Based on data from 20 people who took the Breakroom Quiz between December 2024 and April 2026.

At Wintrust, are sick days and vacation days separate paid time off?

Sick days and vacation days are separate paid time off.
70% of people say they don’t have to use vacation days when they’re out sick.
Based on data from 10 people who took the Breakroom Quiz between June 2025 and April 2026.

Is the health insurance from Wintrust affordable enough for their workers?

Most people say the health insurance costs are okay.
88% of people say the health insurance costs are okay
Based on data from 16 people who took the Breakroom Quiz between April 2025 and February 2026.

Do people get paid time off at Wintrust?

Most people get paid time off work.
91% of people say they get paid time off.
Based on data from 11 people who took the Breakroom Quiz between June 2025 and April 2026.

How far ahead of time do people find out their work schedule?

Only some people find out their schedule four weeks ahead of time.
  • 30% of people with changing schedules find out their shifts one week or less ahead of time.
  • 10% of people with changing schedules find out their shifts two weeks ahead of time.
  • 20% of people with changing schedules find out their shifts three weeks ahead of time.
  • 40% of people with changing schedules find out their shifts four weeks or more ahead of time.

Based on data from 10 people who took the Breakroom Quiz between December 2024 and December 2025.

Do workers at Wintrust worry about hours?

Most people don’t worry about getting enough hours.
100% of people report they don’t worry about getting enough hours.
Based on data from 14 people who took the Breakroom Quiz between December 2024 and December 2025.

Do Wintrust workers get to choose the shifts they work?

Most people get to choose which shifts they work.
69% report that they have enough control over which shifts they work.
Based on data from 13 people who took the Breakroom Quiz between December 2024 and December 2025.

How easy is it for Wintrust workers to change shifts?

Most people find it easy to change shifts.
100% of people report that it’s easy to change shifts if they need to.
Based on data from 10 people who took the Breakroom Quiz between December 2024 and December 2025.

How easy is it to get time off at Wintrust?

Most people find it easy to get time off.
100% of people report it’s easy to get time off.
Based on data from 17 people who took the Breakroom Quiz between December 2024 and April 2026.

Do Wintrust managers change schedules at the last minute?

Most managers don’t change people’s schedules at the last minute.
100% of people say their manager doesn’t change their shift schedule at the last minute.
Based on data from 14 people who took the Breakroom Quiz between January 2025 and December 2025.

Do jobs at Wintrust spill into time workers aren’t paid for?

Rarely. The job doesn't usually spill into unpaid time.
8% of people report that their job takes up time that they don’t get paid for.
Based on data from 12 people who took the Breakroom Quiz between December 2024 and December 2025.

How easy is it to take sick days at Wintrust?

Most people find it easy to take sick days.
95% of people report that it’s easy to take time off if they are sick.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Is working at Wintrust good if you’re a parent or caregiver?

Most parents and caregivers say this is a good place to work.
100% of people who care for a child or other relative report this is a good place to work.
Based on data from 5 people who took the Breakroom Quiz between January 2025 and February 2026.

Do people at Wintrust feel treated with respect by their managers?

Most people feel treated with respect by their managers.
95% of people say they’re treated with respect by their managers.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people at Wintrust get to take their breaks without interruption?

Most people get breaks without interruption.
89% of people report that they get to take their breaks without interruption.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Is it stressful to work at Wintrust?

Most people feel stressed here.
78% of people say they often feel stressed at work.
Based on data from 18 people who took the Breakroom Quiz between January 2025 and April 2026.

Do people at Wintrust enjoy their jobs?

Only some people enjoy their job.
47% of people report they don’t enjoy their job.
Based on data from 17 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people at Wintrust recommend working with their team?

Only some people recommend working with their team.
55% of people report that they wouldn’t recommend working with their immediate team to a friend.
Based on data from 20 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people get enough training when they start at Wintrust?

Some people didn’t get enough training when they started.
37% of people report they didn’t get enough training when they started working here.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people get support to advance at Wintrust?

Most people are given support to advance their career here.
In the last year, 69% of people report being given support to advance their career here.
Based on data from 16 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people think Wintrust’s headquarters understands what’s happening where they work?

Some people think headquarters doesn’t understand what’s happening where they work.
65% of people think that this employer’s headquarters or owners don’t have a good understanding of what’s really happening where they work.
Based on data from 17 people who took the Breakroom Quiz between January 2025 and April 2026.

Do workers feel well informed about how Wintrust is doing?

Most people feel well informed about how the company is doing.
72% of people feel that they are kept well informed about how the company is doing as a whole.
Based on data from 18 people who took the Breakroom Quiz between December 2024 and April 2026.

What other companies are hiring for Human Resources Manager jobs?

What are the most popular jobs at Wintrust Financial?

VP, Business Strategy - WLF

Wintrust

Rosemont, IL • On-site

$98K - $132K/yr

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 4 days ago

Wintrust rating

8.0

Company rating: 8.0 out of 10

Based on 20 frontline employees who took The Breakroom Quiz

72nd of 174 rated banks

Job description

As the largest life insurance premium finance company in the country, Wintrust Life Finance provides customized financing solutions to qualified borrowers seeking to finance their life insurance premiums. Our financing solutions have supported numerous planning structures, including traditional wealth transfer, key-man insurance, buy-sell arrangements, split dollar arrangements, term alternatives, charitable giving, income replacement strategies, and more. Wintrust Life Finance is a subsidiary of Wintrust, a financial services company with more than $66 billion in assets.
The WLF VP, Business Strategy, is responsible for collaborating with key stakeholders in the analysis, formulation and execution of WLF's strategic plan. Key aspects of this position focus on completing life premium finance market research, analysis, reporting, strategic initiative development, project & product management, and delivering regularly scheduled reports and presentations in collaboration with department EVP.
What You'll Do
Strategy & Strategic Planning:
  • Manage WLFs process efficiency and strategy administration team
  • Collect and analyze premium finance data related to strategic plan and generate insights to initiate strategic development activities
  • Complete regularly scheduled market research in support of strategic plan
  • Collaborate with departments to evaluate operations to identify growth and development opportunities
  • Monitor and evaluate the performance of the company's strategies, initiatives, and objectives and report findings to executive leaders
  • Help drive decision making resulting in medium- and long-term process improvements
  • Proactively present business findings, projections and make recommendations to department EVP and other leaders as appropriate
  • Support EVP in developing and communicating WLFs strategic initiatives, including but not limited to presentations, financial reports, and models in both written and verbal formats
  • Lead effective, efficient meetings with clients, prospects, and WLFs Strategic Initiative Owners to drive strategic plan efforts
  • In conjunctions with department EVP, act as an internal dot connector, working with project managers to ensure internal resources are collaborative and projects/work streams are on time and in line with expectations
  • Partner with WLFs Strategic Initiative Owners, Wintrust's ePMO and Wintrust Oversight teams (ePMO, TPRM, IC, CC, IPA, ASRB and InfoSec) to drive strategic level project approval and implementation

Product Development & WLF Business Line Support:
  • Drive internal understanding of key customer personas and engage with clients/prospects to better understand workflows. Synthesize learnings to internal stakeholders to drive and facilitate loan growth
  • Partner with Sales, Sales Leadership and Client Success teams to define, enhance, track and drive product adoption
  • Through the lens of the Strategic Plan build Product Level KPIs to define, monitor and manage success
  • Support optimization modeling and process planning in collaboration with team level management, outside sales and internal stakeholders. Evaluate premium tiers for client/prospects, calculate quote conversation ratios, average down payments, installments, and price to deliver actionable recommendations in identifying growth opportunities

Foster a culture of collaboration and process improvement:
  • Look for opportunities, identify gaps and scale efficiencies and new ways of working across multiple projects and environments
  • Influence and facilitate the creation of long-term relationships with other departments and vendors
  • Source data to make compelling and tangible recommendations of a future state for the organization
  • Leverage relationships and organizational values to prioritize outcomes effectively
  • Employ practical methods and action steps to move the organization toward the strategic vision
  • Help Identify obstacles to transformation and challenge conventional thinking

Qualifications
  • 10-15 years of experience in the Financial Industry
  • Premium Financial experience preferred
  • Experience owning a strategic initiative from concept to completion
  • Bachelor's Degree required
  • MBA Preferred
  • Onsite position

Compensation
The estimated salary for this role is $98,000 - $132,000 along with eligibility to earn an annual bonus. Actual pay rate may vary based on several factors, such as a candidate's qualifications, skills and experience
Benefits
Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet Insurance
#LI-ONSITE
#LI-LR1
From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success. Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.

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