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Sikich

Technology-enabled professional services and advisory firm

Industry Growth Leader - Insurance Services

Full-TimeUpdated on 10/23/2026
$161.8k - $275k+ Employee referral bonus + Client referral bonus
Mid
Remote in USA
Remote
Sales & Account ManagementBusiness Development & Partnerships

About the job

Requirements
  • Proven consultative solution-selling experience within the insurance industry, particularly in core system modernization, digital transformation, data and artificial intelligence, and/or 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.
  • Entrepreneurial mindset with strong execution bias, especially in a fast-evolving market.
  • Engage employees, foster their development, and build a positive culture.
  • Identify opportunities in business problems and develop, articulate, and implement solutions.
  • Build relationships across all organizational levels and business units.
  • Follow through on commitments, act with integrity, and be consistent and credible.
  • Gain support for ideas, proposals, and solutions and motivate others to advance initiatives and objectives, with or without formal authority.
Responsibilities
  • Develop and execute a vertical growth strategy to expand Sikich’s 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 Sikich’s differentiated insurance offerings, particularly modernization of client core platforms (ERP, CRM, policy, billing, and claims systems) and their technology ecosystems, including Digital Front Door solutions, financial and operational reporting, data and AI, and compliance enablement.
  • Lead go-to-market strategy and executive positioning for Sikich 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 Sikich’s integrated digital and operational solutions across the insurance lifecycle.
  • Collaborate with leaders across Sikich practices, including Salesforce, Microsoft Business Applications, Data Analytics and AI, 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, from strategy and system selection through implementation, integration, and managed services.
  • Support go-to-market campaigns reinforcing Sikich’s Digital Regulated Industries positioning and thought leadership.
  • Serve as an insurance industry thought leader through webinars, conferences, and industry forums.
  • Monitor emerging trends in underwriting, embedded insurance, delegated authority digitization, regulatory technology, and AI-driven risk insights to inform client conversations and go-to-market evolution.
  • Provide voice-of-the-customer feedback to refine Sikich’s insurance vertical strategy, offerings, and partner ecosystem.
  • Develop an Insurance Playbook spanning Sikich practices and capabilities, including Salesforce (Digital Front Door), Microsoft, Data Analytics and AI, Cybersecurity, Risk Management, and IT Managed Services.
  • Meet performance metrics for insurance vertical pipeline growth and closed revenue across new and existing clients, average spend per insurance client, and cross-practice expansion across Sikich offerings.

About the company

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's Take

What believers are saying

  • April 30, 2026 Jefferson Wells added 300+ employees and $76 million revenue.
  • May 14, 2026 Tantus integration strengthened federal AI, zero trust, and quantum work.
  • October 29, 2025 PLAIO partnership opened pharmaceutical supply-chain AI work.

What critics are saying

  • Three 2026 acquisitions strain integration across Burwood, Jefferson Wells, and Tantus.
  • Federal growth depends on DLA JETS II, DOT SWES, and OASIS+ recompetes.
  • A failed Sikich Federal rollout would erase years of D.C. acquisition spending.

What makes Sikich unique

  • Bain Capital's $250 million 2024 investment funds aggressive acquisition-led expansion.
  • Burwood, Jefferson Wells, and Tantus give Sikich consulting, compliance, tech, and federal depth.
  • Tantus adds DLA JETS II, DOT SWES, and OASIS+ Unrestricted contract access.

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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

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.