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Skyward Business Jobs (NOW HIRING)

$100 - $170/hr

Provide detailed explanations to Skyward A&H clients regarding conditions and requirements of quotes, rating decisions, and other information to support the sale of new and renewal business.

Solutions Architect

Rockville, MD

$64.25 - $84.50/hr

We are Skyward. That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and ...

Solutions Architect

Rockville, MD · On-site

$150K - $190K/yr

We are Skyward. That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and ...

Solutions Architect

Rockville, MD · On-site

$64.25 - $84.50/hr

We are Skyward. That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and ...

Technical Analyst

Rockville, MD · On-site +1

$90K - $100K/yr

We are Skyward. That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and ...

Technical Analyst

Rockville, MD · Remote

$90K - $100K/yr

We are Skyward. That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and ...

Cloud Engineer

Rockville, MD

$56.75 - $76/hr

We are Skyward. That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and ...

$125 - $150/hr

Supports business partners through communication about specific claims, identification of claim ... At Skyward Specialty, we approach insurance differently. Our specialty insurance experts are ...

We are Skyward. That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and ...

Company Description TechStar Group is a niche Product Development, Business Solutions, and global I ... the Skyward Mobile Platform. You will participate in a collaborative Agile team environment and ...

... Skyward's product solutions. This is a hands-on leadership position requiring both deep technical expertise and strong business acumen. The Director of Technology will bridge engineering execution ...

... Skyward's product solutions. This is a hands-on leadership position requiring both deep technical expertise and strong business acumen. The Director of Technology will bridge engineering execution ...

Showing results 21-40

Skyward Business information

See salary details

$19.5K

$69.4K

$179K

How much do skyward business jobs pay per year?

As of Sep 5, 2026, the average yearly pay for skyward business in the United States is $69,377.00, according to ZipRecruiter salary data. Most workers in this role earn between $43,500.00 and $78,500.00 per year, depending on experience, location, and employer.
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What cities are hiring for Skyward Business jobs?

Cities with the most Skyward Business job openings:

What states have the most Skyward Business jobs?

States with the most job openings for Skyward Business jobs include:

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Infographic showing various Skyward Business job openings in the United States as of August 2026, with employment types broken down into 83% Full Time, 14% Part Time, and 3% Contract. Highlights an 90% Physical, 3% Hybrid, and 7% Remote job distribution, with an average salary of $69,377 per year, or $33.4 per hour.

Senior Underwriter or AVP, Medical Stop Loss (Core)

Skyward Specialty Insurance Group

On-site

$100 - $170/hr

Other

Medical, Retirement, PTO

Posted 17 days ago


Key responsibilities

  • Evaluate risk for in-force business and new business prospects, and make decisions to quote or decline to quote.

  • Develop and communicate rate recommendations and decisions for new and renewal business within underwriting authority limits.

  • Manage the book of new and renewal accounts to balance profitability and growth.


Job description

## Senior Underwriter or AVP, Medical Stop Loss (Core)Applylocations: Remote - UStime type: Full timeposted on: Posted Todayjob requisition id: JR218The Senior Underwriter OR AVP is responsible for underwriting new and renewal medical stop-loss accounts at a profitable level. This role involves managing relationships with producers and customers to ensure alignment with overall company stop-loss goals. The Senior Underwriting position works closely with the other team members in the region and with the sales team to identify business and producers that most closely meet our underwriting acumen.**Key Responsibilities:*** Evaluate risk for in-force business and new business prospects. Make decisions to quote or decline to quote and develop premium rates in accordance with underwriting guidelines and authority limits.* Develop and communicate new business or renewal rate recommendations and decisions in line with underwriting authority limits.* Prepare and generate correspondence, proposals, and other reports as needed.* Provide detailed explanations to Skyward A&H clients regarding conditions and requirements of quotes, rating decisions, and other information to support the sale of new and renewal business.* Coordinate medical reviews with the clinical risk management team and make recommendations regarding the level of acceptable risk.* Negotiate rates, terms, and conditions for new and existing business.* Manage the new business and renewal book to balance profitability and growth.* Process sold accounts and confirmed renewals following established procedures.* Develop and maintain relationships with clients, producers, and sales representatives to support the company’s production goals and persistency.* Support Skyward A&H growth initiatives related to reference-based pricing, captive, and small group programs.* Review plan design and calculate rates for requested or recommended plan changes.* Provide competitive feedback on rates, products, pricing, and marketing strategies.* Make presentations to peers, producers, and leadership as necessary.* Utilize departmental tools, experience, and judgment during the underwriting process to set pricing, review risk, negotiate, and accomplish goals.* Assist associate underwriters with training and peer review.* Perform other duties as assigned.* Some travel may be required for trainings and/or meetings (less than 10%).**Continuous Learning and Development:*** Stay current with industry trends, regulatory changes, and competitive landscape to ensure the company remains at the forefront of underwriting practices.* Participate in training sessions and professional development opportunities.**Education & Experience:*** Bachelor’s Degree preferred.* 4+ years of experience underwriting medical stop-loss required.* Preferred experience underwriting reference-based pricing and/or small group programs.* Professional certifications (HIAA, CEBS, FMLI, etc.) beneficial.**Skills:*** In-depth knowledge of underwriting principles, risk assessment, and regulatory requirements.* Proven track record of developing and implementing successful underwriting strategies and policies.* Strong analytical and decision-making skills, with the ability to evaluate complex transactions.* Ability to prioritize and balance a dynamic workload.* Strong communication and interpersonal skills, with the ability to build relationships with internal and external stakeholders.* Proficiency in underwriting software (Connexure/ESL preferred) and other relevant technology.**Compensation & Benefits**The applicable base salary for this opportunity is $100,000 - $170,000. The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. In addition to the base salary, this opportunity may be eligible for performance-based incentives. We are excited to offer a competitive total rewards package which includes health and welfare benefits, tuition and professional certification assistance, 401k savings, elective participation in the Employee Stock Purchase Program, paid time off, paid holidays, and child bonding leave, as well as other employee assistance. #J-18808-Ljbffr