Since 2001, Osage Advisors has helped family and closely held business owners sell the companies they spent a lifetime building. We are a boutique by design: small teams, senior attention on every engagement, and a disciplined, full-process approach to sell-side M&A.
If you want to do meaningful work for owners at the most important moment of their careers, without the bureaucracy of a large bank, we would like to talk.
Benefits
Competitive compensation, health insurance, and a 401(k) retirement plan.
Why Osage?
A boutique by design: small teams and senior attention on every engagement.
A disciplined, full-process approach to sell-side M&A that clients trust.
Meaningful work for family and closely held business owners at a defining moment.
The autonomy of an entrepreneur with the support of an experienced deal team.
Available Positions
Managing Director, Investment Banking
Location: Remote (U.S.), with client travel; headquarters in Connecticut
Osage Advisors is seeking an accomplished Managing Director to originate and lead lower middle market sell-side M&A engagements. The ideal candidate brings 10–15 years of M&A experience, a strong referral network, and a track record of winning mandates and taking them from pitch to close. This is an opportunity to grow with an established platform, with the autonomy of an entrepreneur and the support of an experienced deal team.
What You Will Do
- Originate new sell-side engagements through your referral network and industry relationships.
- Lead engagements from pitch to close: valuation, marketing, buyer outreach, negotiation and closing.
- Serve as the senior advisor and trusted point of contact for business owners.
- Guide and develop the deal team on each engagement.
What You Bring
10–15 years of M&A or investment banking experience, ideally in the lower middle market.
A strong referral network and a track record of winning and closing mandates.
Excellent client, negotiation and communication skills.
Required securities licenses, or the ability to obtain them.
What We Offer
Competitive compensation with meaningful participation in the deals you lead. Health insurance and a 401(k) retirement plan. Remote flexibility within the U.S., with client travel. An established platform and an experienced deal team behind you.
Development Associate
Hybrid, Connecticut office
Osage Advisors is seeking a driven, detail-oriented Development Associate to support the firm’s business development and deal marketing efforts. Working directly with the firm’s President, you will see how lower middle market M&A engagements are won and executed, with exposure to clients across a wide range of industries. This is a hands-on role for someone early in their career who wants to learn the business from the ground up, on a small team where your work matters from day one.
What You Will Do
Business Development
- Prepare pitch materials and presentations for prospective clients
- Identify and evaluate potential acquirers and targets
- Support the firm’s marketing and thought leadership, including blogs, podcasts, and social media
Deal Marketing
- Execute deal-related email campaigns to targeted buyer groups
- Coordinate and track confidentiality agreements (CAs) and Confidential Information Memorandum (CIM) distribution
- Track buyer activity and follow-up throughout the marketing process
Deal Team and Systems Support
- Administer Salesforce and prepare pipeline and activity reports
- Provide daily support to deal teams across active engagements
What You Bring
- 2–3 years of experience, preferably in investment banking, private equity, corporate development, or another M&A-related field
- Bachelor’s degree; finance, economics, business, or marketing preferred
- Strong analytical, research, and organizational skills, with close attention to detail
- Proficiency in Excel, PowerPoint, and Word, as well as AI tools such as Microsoft Copilot or Claude
- A strong work ethic, the ability to manage multiple priorities, and discretion with confidential information
- Clear written and verbal communication
- Experience with Salesforce, Salesforce Account Engagement, or Dropbox Sign a plus
What We Offer
- Direct access: work alongside the firm’s President and senior deal team
- Broad exposure: engagements across many industries and every stage of the sell-side process
- Career growth: hands-on experience that builds a foundation for a career in M&A
- Rewarding compensation: competitive salary and performance-based bonuses
- Benefits: health insurance and a 401(k) retirement plan
- Flexibility: a hybrid schedule based in our Connecticut office
How to Apply
Submit your application through our career form, or send your resume with a brief note describing your referral network and representative transactions. Confidential inquiries are welcome.
Osage Advisors is an equal opportunity employer.
Certain principals of Osage Advisors are registered representatives with StillPoint Capital, LLC, Member FINRA/SIPC, Tampa, FL.
