Full-Time

Industry Growth Leader

Insurance Services

Sikich

Sikich

1,001-5,000 employees

Technology-enabled professional services and advisory firm

Compensation Overview

$161.8k - $275k/yr

Remote in USA

Remote

Category
Business & Strategy (1)
Required Skills
ERP
CRM
Cybersecurity
Salesforce
Risk Management
Data Analysis

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Requirements
  • Proven consultative solution-selling experience within the insurance industry, particularly in core system modernization, digital transformation, data and artificial intelligence, and regulatory-driven initiatives.
  • Strong understanding of regulatory, operational, and technology challenges facing insurance companies, including emerging, mid-market, and enterprise carriers, managing general agents, and specialty insurance organizations.
  • Executive-level communication, presence, and credibility with C-suite and senior insurance stakeholders, including chief information officers, chief operating officers, chief underwriting officers, and heads of distribution.
  • An entrepreneurial mindset with a strong execution bias, especially in a fast-evolving market.
Responsibilities
  • Develop and execute a vertical growth strategy to expand market share across carriers, managing general agents, wholesalers, reinsurers, and specialty insurance organizations.
  • Drive strategic pursuits and pipeline expansion by aligning sales plays to insurance-specific challenges, including core system modernization, underwriting transformation, delegated authority oversight, digital distribution, regulatory compliance, and data-driven decision-making.
  • Support account teams with deal shaping, executive positioning, and value articulation for complex, multi-solution opportunities.
  • Champion differentiated insurance offerings, particularly modernization of client core platforms and their technology ecosystems, including enterprise resource planning, customer relationship management, policy, billing, and claims systems, Digital Front Door solutions, financial and operational reporting, data and artificial intelligence, and compliance enablement.
  • Lead go-to-market strategy and executive positioning for technology solutions such as Digital Front Door for Insurance, a Salesforce-based solution that streamlines quoting, submissions, policy servicing, and agent and broker engagement and integrates with existing policy administration systems.
  • Translate technical capabilities into measurable business outcomes for insurance executives and communicate the value of integrated digital and operational solutions across the insurance lifecycle.
  • Collaborate with leaders across Salesforce, Microsoft Business Applications, Data Analytics and Artificial Intelligence, Cybersecurity, and Risk Management to design and pursue coordinated account strategies aligned to insurance modernization roadmaps.
  • Expand wallet share within existing insurance clients through end-to-end transformation programs spanning strategy, system selection, implementation, integration, and managed services.
  • Support go-to-market campaigns reinforcing the Digital Regulated Industries positioning.
  • Serve as an insurance industry thought leader through webinars, conferences, and industry forums.
  • Stay ahead of emerging trends in underwriting, embedded insurance, delegated authority digitization, regulatory technology, and artificial-intelligence-driven risk insights to inform client conversations and go-to-market evolution.
  • Provide voice-of-the-customer feedback to refine the insurance vertical strategy, offerings, and partner ecosystem.
  • Track insurance vertical pipeline growth, closed revenue, average spend per insurance client, and cross-practice expansion.
  • Develop an Insurance Playbook spanning Sikich practices and capabilities, including Salesforce Digital Front Door, Microsoft, Data Analytics and Artificial Intelligence, Cybersecurity, Risk Management, and information technology managed services.

Sikich is a global professional services firm that uses technology-enabled solutions to help clients improve performance. It combines audit, tax, and business advisory services with a broad portfolio of technology offerings to deliver digital strategies for corporations, nonprofit organizations, and government entities. Audits and attest services are provided by Sikich CPA LLC, while tax and advisory work come from Sikich LLC and its subsidiaries. The company operates under an alternative practice structure, where each Sikich entity is independently owned and only liable for its own services. Sikich differentiates itself by offering a wide range of technology-enabled professional services through a large, multi-discipline team and by serving a diverse client base across public and private sectors. Its goal is to help clients achieve long-term, strategic outcomes and improved performance through practical, technology-driven solutions and expert guidance.

Company Size

1,001-5,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Naperville, Illinois

Founded

1982

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Simplify Jobs

Simplify's Take

What believers are saying

  • Jefferson Wells added 300 employees and $76 million revenue on April 30, 2026.
  • Burwood deepens cloud, security, and AI delivery across healthcare and higher education.
  • Sikich's headcount reached 11,453 in 2025, up 5.3% from 2024.

What critics are saying

  • Hilco Diligence's trade-secret case survived dismissal in May 2025.
  • Three 2026 acquisitions strain integration across Burwood, Jefferson Wells, and Tantus.
  • Federal contract losses after Tantus cripple Sikich's growth thesis by 2027.

What makes Sikich unique

  • Sikich now spans federal, AI, compliance, and consulting after Burwood, Jefferson Wells, and Tantus.
  • Bain Capital's $250 million backing funds acquisitions while Sikich keeps majority control.
  • Tantus brings DLA JETS II, DOT SWES, and OASIS+ Unrestricted into Sikich Federal.

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Benefits

Health Insurance

Flexible Work Hours

Unlimited Paid Time Off

Paid Vacation

Paid Holidays

Hybrid Work Options

Wellness Program

401(k) Retirement Plan

401(k) Company Match

Parental Leave

Tuition Reimbursement

Pet Insurance

Employee Referral Bonus

Company News

OrangeSlices AI
Jun 24th, 2026
Tantus Technologies to become Sikich Federal as post-acquisition integration nears completion

Tantus Technologies is transitioning to Sikich Federal following its acquisition by Sikich LLC. Karlene Stecchi, former president of Tantus, now serves as Principal, Gov Tech Lead at Sikich, overseeing federal technology initiatives including government modernisation, cybersecurity, AI, and quantum technologies. The integration has been underway for over a year, with Sikich branding increasingly visible at federal events and client engagements. Tantus brings contract vehicles including DLA JETS II, DOT SWES, and OASIS+ Unrestricted, along with past performance across Treasury, USDA, Department of Transportation, NIH, and CMS. The rebrand signals a shift from quiet integration to an active market-facing strategy. The combined organisation now has expanded contract access and delivery capabilities spanning both federal and commercial markets, positioning it to compete more aggressively in the federal sector.

Sikich
May 14th, 2026
Sikich finalizes integration of Tantus Technologies - Sikich

Sikich announced it is finalizing its integration of Tantus Technologies, a Virginia-based company providing innovative technologies to federal government agencies.

Associated Press
Apr 30th, 2026
Sikich acquires Jefferson Wells U.S. for $100M, adding 300+ employees and $76M in revenue

Sikich, a professional services company, has acquired Jefferson Wells' US operations from ManpowerGroup for $100 million, with net cash proceeds of approximately $89 million after adjustments. The deal brings 300 employees and adds capabilities in risk and compliance, finance and accounting, and tax consulting. Milwaukee-based Jefferson Wells, with over 30 years of operating history, generated $76 million in US revenues in 2025. The company serves public and highly regulated companies across financial services, technology and energy sectors, complementing Sikich's existing presence in healthcare, life sciences and manufacturing. Sikich chairman Christopher Geier said the acquisition enhances existing capabilities whilst maintaining alignment in culture and client service approach. The transaction closed on 30 April.

PR Newswire
Apr 30th, 2026
ManpowerGroup sells Jefferson Wells US to Sikich for $100M

ManpowerGroup has sold its Jefferson Wells US business to professional services firm Sikich for $100 million. The transaction closed on 30 April 2026, with ManpowerGroup receiving net cash proceeds of approximately $88 million after working capital adjustments. Jefferson Wells US delivers risk and compliance, finance and accounting, and tax solutions through project consulting, integrated resourcing and executive search. The business generated $76 million in revenues in 2025. ManpowerGroup plans to use the proceeds to strengthen its balance sheet whilst focusing on its core Manpower, Experis and Talent Solutions brands. The sale will result in a gain to be recognised in the second quarter. Sikich said the acquisition enhances its capabilities in risk, compliance, finance, accounting and tax services.

Yahoo Finance
Apr 7th, 2026
Sikich acquires IT consulting firm Burwood Group to strengthen tech offerings

Sikich, a professional services company specialising in consulting, technology and compliance, has acquired Burwood Group, a Chicago-based IT consulting and integration firm with nearly 30 years' experience. The acquisition strengthens Sikich's technology capabilities across healthcare, higher education, industrials and financial services sectors. Burwood Group brings expertise in IT security and platform modernisation to help organisations work more efficiently. Combined with Sikich's business advisory capabilities, the partnership will offer clients end-to-end solutions across business, technology and governance. "Burwood Group brings a strong pedigree and track record in anticipating what customers need," said Sikich CEO Christopher Geier. The companies share complementary digital transformation offerings and cultural alignment. Sikich operates approximately 2,000 team members across North America, EMEA and APAC.