A Chicago-based private investment firm, Gray Capital Investors looks to leverage decades of experience in real estate, construction, related-technology, and industries to invest with operators in those areas.
 
As an entirely family-owned and managed fund, Gray Capital brings flexibility, an ability to make quick decisions, and a long-term perspective.

Industry: Investment Management
Company Size: 2-10 employees

Gray Capital Investors

Savvy Admin PROD

We are seeking a highly organized, proactive, and hands-on Digital Marketing Specialist to support branding, investor communications, and deal-related marketing efforts. This role will be instrumental in building a consistent, professional market presence - ideal for someone who thrives in an entrepreneurial environment and is comfortable wearing multiple hats.

**Key Responsibilities **

- Coordinate with internal partners to maintain and update WordPress website, including case studies, news updates, job postings, and other relevant content.

- Develop relevant and timely content for digital platforms, including social media, email campaigns, blogs, etc.

- Maintain and update company presentations, pitch decks, and marketing collateral.

- Assist with CRM maintenance and marketing automation processes (Salesforce) to manage campaigns and outreach.

- Manage email marketing including content development, design, distribution lists and analytics.

- Tightly manage social media calendar and develop content while ensuring brand consistency and obtaining approvals when necessary.

- Coordinate with outside vendors, including AV teams, PR and marketing firms, etc.

- Provide event support with pre-event and post-event communications and other activities related to clients and key partners as needed.

- Support onboarding of new staff and coordination of visiting team members.

- Other duties as assigned.

**Qualifications **

- Bachelor’s degree in Business, Marketing, Communications, or related field preferred.

- 3-5 years of experience in marketing, preferably in real estate, finance, or professional services.

- Strong organizational and project management skills.

- Excellent writing and editing skills as well as verbal communication skills.

- Proficiency in Microsoft Office (Teams, Outlook, Word, Excel, PowerPoint), CRM tools, and other presentation software.

- Experience with content management systems (SalesForce) and social media platforms strongly preferred.

- Working knowledge of marketing tools such as:

- Email marketing platforms (e.g., Mailchimp, HubSpot)

- Basic graphic design tools (e.g., Canva, Adobe Creative Suite preferred)

- Basic graphic design/video editing capabilities for video for social, adding logos and graphics, taking high quality photos and video, editing templates is a plus.

- High level of attention to detail, and the ability to manage multiple priorities in a fast-paced, high-visibility environment.

- A strong sense of urgency and a positive, proactive desire to support a broad range of initiatives and tasks and an ability to work proactively, prioritizing and managing time independently.

- To be polished, professional, and able to comfortably interact effectively with managers, clients, and C-Suite executives.

Digital Marketing Specialist

With more than $1 billion in premium, SageSure, the largest residential property insurance managing general underwriter (MGU) in the United States, is pioneering the ways people protect their American Dream. 

As a leader in catastrophe-exposed property insurance, we deliver reliable coverage, exceptional customer experiences, and strong underwriting results in challenging insurance markets across 14 states. We offer home, flood, and commercial coverage on behalf of our highly rated carrier partners.  

We have more than 600 employees across nine offices—Jersey City, NJ; Mountain View, CA; Atlanta, GA; Chicago, IL; Tallahassee, FL; Cincinnati, OH; Houston, TX; Mt. Laurel, NJ; and Cheshire, CT, and remote locations—who are tackling the industry’s toughest challenges.    

Our nimble, highly responsive culture nurtures critical thinkers who run toward problems and engineer solutions. We relentlessly pursue better outcomes by investing in the technology, talent, and tools that position us to succeed in demanding markets. To learn more, visit sagesure.com.

Industry: Insurance
Company Size: 501-1,000 employees

SageSure

**Overview: **

If you're looking for the stability of a profitable, growing company with the entrepreneurial spirit of a startup, we’re hiring. SageSure, a leader in catastrophe-exposed property insurance, is seeking a **Senior Catastrophe Risk Analyst. **

In this role, you’ll play a critical part in advancing the scientific, statistical, and model-based understanding of catastrophe risk across perils such as hurricanes, earthquakes, wildfires, floods, and severe convective storms. You’ll support the development and evaluation of catastrophe models, enhance internal risk views, and deliver insights to inform underwriting, portfolio management, and reinsurance strategy.

**What you’d be doing: **

- Evaluate third-party catastrophe models (e.g., RMS, Verisk, CoreLogic) and contribute to the development of internal risk views.

- Analyze large datasets (e.g., exposure data, claims data, hazard data) to assess model performance, validate assumptions, and identify improvement areas.

- Conduct claims analysis, event response, and post-event analytics.

- Support integration of climate science and emerging research into catastrophe risk analytics.

- Collaborate with internal stakeholders (underwriting, actuarial, reinsurance, risk, and data science teams) to apply research findings to business decisions.

- Design and implement tools, frameworks, or methodologies that improve model transparency and interpretability.

- Monitor and interpret academic, regulatory, and industry developments in catastrophe risk science and modeling.

- Ad hoc job duties as assigned.

**We’re looking for someone who has: **

- Advanced degree (Master’s or PhD) in Atmospheric Science, Hydrology, Earth Science, Engineering, Applied Mathematics, Statistics, or a related quantitative field.

- 5+ years of experience in catastrophe modeling, natural hazard risk research, insurance analytics, or a related field.

- Proficiency with catastrophe modeling platforms (RMS, Verisk, AIR, etc.).

- Strong coding and data analysis skills (e.g., Python, R, SQL).

- Experience working with geospatial data and tools (e.g., GIS, QGIS, ArcGIS).

- Familiarity with stochastic simulation, probabilistic risk modeling, and related statistical methods.

- Strong critical thinking, problem-solving, and research skills.

- Excellent communication skills with the ability to explain complex concepts to non-technical audiences.

- Proven ability to work collaboratively in cross-functional, research-driven environments.

**Highly preferred candidates also have: **

- Experience in the (re)insurance, ILS, consulting, or catastrophe model vendor environment.

- Experience developing internal catastrophe models or integrating third-party models into portfolio management workflows.

- Familiarity with climate risk modeling and emerging methodologies in catastrophe risk R&D.

- Demonstrated track record of publishing or presenting research in the field of natural hazard modeling or risk analytics.

**Catastrophe Risk R&D: **

At SageSure, the Catastrophe Risk R&D team is redefining how the industry understands and manages catastrophe risk. We operate at the intersection of science, technology, data, and industry insight, developing a proprietary view of risk that goes beyond traditional models. Our work shapes risk management strategy, capital allocation, and external market positioning, directly influencing how SageSure protects policyholders and partners in catastrophe-exposed regions.

Join the team that sees risk differently—and proves it.

**About SageSure: **

Named among the Best Places to Work in Insurance by Business Insurance for four years in a row (2020-2023), SageSure is one of the largest managing general underwriters (MGU) focused on catastrophe-exposed property in the US. Since its founding in 2009, SageSure has experienced exceptional growth while generating underwriting profits for carrier partners through hurricanes, wildfires, and hail. Available in 16 states, SageSure offers more than 110 home, flood, and commercial products on behalf of its highly rated carrier partners. Today, SageSure manages more than $3.2 billion of inforce premium and helps protect more than 970,000 policyholders.

We have more than 1,000 employees in a distributed workforce environment across 12 offices—Fairfield, CA; Mountain View, CA; Cheshire, CT; Jacksonville, FL; Tallahassee, FL; Tampa, FL; Chicago, IL; Jersey City, NJ; Marlton, NJ; Cincinnati, OH; Houston, TX; Sheboygan, WI—who are tackling the industry’s toughest challenges.

SageSure is a proud Equal Opportunity Employer committed to building a workforce that reflects the spectrum of perspectives, experiences, and abilities of the world we live in. We recognize that our differences make us strong, and we actively seek out diverse candidates through partnerships with organizations, institutions and communities that represent various backgrounds. We champion belonging and inclusion for all identities, including, but not limited to, race, ethnicity, religion, sexual orientation, age, veteran status, ability status, gender, and country of origin, striving to create a culture where all individuals feel valued, respected, and empowered to bring their authentic selves to work.

Our nimble, highly responsive culture nurtures critical thinkers who run toward problems and engineer solutions. We relentlessly pursue better outcomes by investing in the technology, talent, and tools that position us to succeed in demanding markets. Come join our team! Visit sagesure.com/careers to find a position for you.

**California Applicants: ** View SageSure’s Workforce Members’ Privacy Notice - CA Privacy Policy & Notice of Collection

Senior Catastrophe Risk Analyst

We build world-class software companies with values-driven founders.

FutureSight is a leading venture studio that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale.

Industry: Venture Capital and Private Equity Principals
Company Size: 11-50 employees

FutureSight

**The Opportunity**

FutureSight is seeking a Co-Founder & CEO to lead Veriflow, an AI-native denial management and revenue recovery venture currently being built at our studio. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.

We are entering a $16B+ Total Addressable Market with a gaping $ 7.5B-$10B whitespace, targeting the highly underserved mid-market segment. Currently, 30-40% of denied medical claims go uncontested because practices lack the staff and capital to contest them. This systemic failure leaves between $50,000 and $300,000 in legally earned revenue permanently abandoned at each practice every year.

Veriflow AI resolves denied and aged claims end-to-end, embedding outcome-based contingency pricing—meaning practices pay zero upfront, and we only take a cut of the dollars we successfully recover, for our target ideal customer profile (practices with $80K+ in annual recoverable claims).

**Market Context**

We didn't just read market reports; we spent weeks interviewing billing managers, practice owners, revenue cycle leaders at health systems, and even digital operations leaders at major insurance companies. The dysfunction we uncovered is staggering, creating a massive opportunity for a disruptor:

- The pain is so severe, practices are building their own tech: The frustration of payer opacity is so deep that medical billers are hiring part-time software engineers to build in-house robotic process automation (RPA) scrapers just to check claim statuses

- Massive, emotional write-offs: Staff carry immense guilt over these administrative losses. One small-practice assistant admitted, "I feel like we probably had to write off probably close to a million dollars" simply because they couldn't keep up with the manual follow-ups

- The "Payer-Side Inversion" Opportunity: We discovered that insurance companies are drowning in the exact same claims dysfunction they generate. One major payer we interviewed reported a backlog of 31,000 contested claims that consumed 80% of their staff's operational capacity, forcing emergency hires just to manage the disputes

- The Competition is Distracted: Well-funded Tier-1 competitors are charging $15K+ upfront licensing fees and fighting over enterprise health systems. The competitive window to capture the mid-market with a contingency-priced autonomous agent is wide open

**About FutureSight**

FutureSight is a leading venture studio that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale.

You'll co-create with a proven studio team, including:

- John Carbrey - 4x founder, bootstrapped to $100M ARR

- Joshua Auslander - Seasoned CFO and strategic advisor with $200M aggregate exits

- Alan Smith - Globally recognized early stage validation expert, 24 products launched, an exit, 5M+ books sold

- Prathna Ramesh - Early-stage investor and capital strategy advisor

**The Partnership**

- Founder equity with meaningful ownership from inception

- Pre-seed capital committed by FutureSight for early hires and MVP development, with potential for follow-on funding

- Studio resources, including embedded design, engineering, growth, and fundraising support from day one

- Investor and advisor network across healthtech and early-stage capital markets

- A true co-creation model in which you operate as CEO with the studio as your partner

**What You'll Own**

As Co-Founder & CEO, you will set the venture's direction and lead its execution.

- Strategy — Refine the ICP, pricing model, and product positioning

- Customer Development — Lead pilots with practice owners and revenue cycle leaders, convert them to paid engagements, and build the go-to-market motion

- Product — Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback

- Capital — Lead the seed raise, supported by FutureSight's network and traction

- Team — Recruit and lead the founding team, and establish the cultural foundation of the company

**Co-Founder Profile**

- Domain & Workflow Depth: You have direct exposure to healthcare revenue cycle, medical billing, or denial management. You understand the nuanced differences in denial codes, know why administrative denials (like credentialing gaps) are uniquely painful, and intuitively understand the fragmented systems (e.g., Tebra, eClinicalWorks, Availity) that billers are forced to use

- Previous founding experience at a venture-backed company

- Demonstrated success in B2B SaaS go-to-market, including sales and customer engagement

- Fundraising fluency, with the ability to develop investor narratives and close capital

- Proven ability to attract, develop, and retain top talent

- Clear-eyed understanding of the risks and demands of co-founding a venture-backed company

**How to Apply**

Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.

FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.

Co-Founder & CEO - HealthTech - AI Revenue Recovery

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