Full-Time
Senior Operations Specialist
Director
Posted on 2/21/2026
Guggenheim
1,001-5,000 employees
Late-growth, mature-stage global investor
Compensation Overview
$100k - $200k/yr
Company Does Not Provide H1B Sponsorship
Chicago, IL, USA
Hybrid
In-office presence required 3-4 days per week in Chicago.
 Operations & Logistics (1) |
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- Completion of a bachelor’s degree is required.
- Minimum of 8 years of experience in operations, middle office, or treasury functions within financial services, ideally with exposure to trading and structured funding.
- Trade Lifecycle Management: Oversee the full lifecycle of trading and structured funding transactions, from trade capture and affirmation through settlement, collateral, and reconciliations.
- Transaction Booking: Ensure accurate and timely booking of transactions into trade capture, risk, and accounting systems, maintaining consistency across front-to-back platforms.
- Structured Funding Operations: Support bespoke financing and liquidity solutions, including repo, securities lending, derivatives, and structured note issuances.
- Risk & Control Oversight: Maintain robust control frameworks to ensure compliance with regulatory requirements, internal policies, and market standards. Proactively identify, escalate, and resolve operational risks.
- Process Optimization: Lead initiatives to streamline workflows, automate processes, and enhance operational resiliency across funding and trading businesses.
- Stakeholder Partnership: Collaborate with traders, structurers, treasury, legal, compliance, and technology teams to enable smooth execution of complex transactions.
- Regulatory Reporting & Compliance: Ensure accuracy and timeliness in regulatory submissions, disclosures, and funding-related reporting.
- Leadership & Mentorship: Provide guidance to junior team members, fostering professional growth and promoting a culture of accountability and excellence.
- Strong knowledge of products such as repos, securities lending, derivatives, commercial paper, and other funding instruments.
- Proven expertise in trade lifecycle management, transaction booking into both trade capture and accounting systems, collateral management, and settlement processes.
- Solid understanding of regulatory requirements, and comfort operating in a regulated environment.
- Excellent problem-solving, analytical, and organizational skills with meticulous attention to detail.
- Strong interpersonal and communication skills with ability to influence and partner across teams.
- Proficiency with trade capture and accounting systems, as well as advanced Excel and data analysis tools.
Guggenheim provides growth capital by investing $5–$10 million in late-stage companies with 1,001–5,000 employees. It focuses on regional and global markets including the UAE, India, Hong Kong, Chicago, New York, Dubai, London, Mumbai, and the UK. The firm typically funds a single mid-to-large investment per deal to help a company scale, with potential follow-on support if needed. Its goal is to help growing companies expand and achieve returns for its investors by sticking to a defined niche of growth-stage firms and specific deal sizes.
Company Size
1,001-5,000
Company Stage
N/A
Total Funding
$2.1B
Headquarters
Chicago, Illinois
Founded
1999
Simplify's Take
What believers are saying
- Raised $8.4B Private Debt Fund IV, building on $33B invested across 550 borrowers since 2002.
- Hired Simeon Siegel with 20 years experience to boost consumer equity research and deal sourcing.
- Upgraded Datadog to Buy with $175 target, capitalizing on cloud-AI migration trends.
What critics are saying
- J.P. Morgan poaches talent like Mell, eroding retail-tech IB client relationships within 6-12 months.
- Middle-market defaults slash returns on $8.4B Fund IV where Guggenheim leads 90% investments in 12-24 months.
- UAE-Dubai regulators delay $5M-$10M deals via tightened foreign investment rules in 6-12 months.
What makes Guggenheim unique
- Guggenheim invests $5M-$10M in late growth-stage firms with 1001-5000 employees across UAE, India, Hong Kong.
- Closed $8.4B Private Debt Fund IV exceeding hard cap, leading 90% of investments in middle-market loans.
- Guggenheim Securities hires experts like David Mell and Joel Fishbein for retail and tech IB expansion.
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Benefits
Performance Bonus
Company News
Slate Auto, an electric vehicle startup backed by Jeff Bezos, has raised $650 million in Series C funding led by TWG Global to develop an affordable electric pickup truck targeting a mid-$20,000 price point. The company aims to begin US deliveries by year-end. The Troy, Michigan-based startup plans a stripped-down, two-seater pickup with 150 or 240 miles of range. Over 160,000 people have placed $50 refundable deposits. Online orders will open in June, when exact pricing will be announced. Slate is investing $400 million to convert an idled Indiana printing plant for vehicle production. In March, the company appointed Peter Faricy, an Amazon veteran and former SunPower CEO, as chief executive. Other investors include General Catalyst Partners and Slauson & Co.
Guggenheim has upgraded Datadog to Buy with a $175 price target, viewing the stock's 14.33% year-to-date decline as an attractive entry point. The upgrade centres on Datadog's positioning at the intersection of cloud migration and AI deployment. Datadog reported strong fourth-quarter fiscal 2025 results, with revenue of $953.19 million beating estimates by 3.76%. Full-year revenue reached $3.43 billion, up 28% year-over-year. The company now has 603 customers generating over $1 million in annual recurring revenue, up 31% year-over-year. The cloud monitoring platform provider's shares currently trade near $114, well below the 52-week high of $201.69. Management has guided fiscal 2026 revenue to between $4.06 billion and $4.10 billion. Forty-three analysts rate the stock a Buy.
Brian Sir passes the torch. After five years of faithful service as board chair, Brian Sir, formerly the Chief Operating Officer at Guggenheim Partners, is transitioning into the role of committee member. Brian has had an immeasurable impact in his role. Throughout these five years, he's guided Hope during seasons of growth as well as those of challenge. He has also been a source of support and friendship to many on staff. Above all, Brian has been one of Hope's most passionate advocates - especially for its students, families, and teachers. His leadership helped further shape Hope as a place deeply committed to inclusion, community service, and opportunity for all. Under Brian's leadership, Hope launched the Trades Pathway with the support of local unions, initiated its annual spring luncheon, forged a beautiful partnership with Special Children's Charities, invested in the celebration of women's sports programs, led the recruitment and engagement of new board members, developed its board governance committees, and expanded its Career Advancement programs. But just as importantly, Brian made it a priority to support and retain great teachers. During his tenure, Hope reached the highest levels of teacher retention in its two decades of existence - a reflection of a culture where teachers feel valued, supported, and committed to the mission. Chicagohopeacademy is profoundly grateful for Brian's vision and unwavering belief in the transformative power of a Hope education. While his role is changing, Chicagohopeacademy know his commitment to Hope does not. Matt Gerdes is a Principal and Managing Director at Freeport Financial Partners LLC, a Chicago-based investment management firm. Matt steps into the role of chair after two years on the board, serving on the finance, investments, and trades committees. He is responsible for structuring and managing middle-market private credit investments for Freeport's funds and is a member of the firm's investment and management committees. Matt graduated with a B.S. in Finance from Northern Illinois University and holds an M.B.A. from the University of Illinois at Urbana-Champaign. He and his wife, Jennifer, reside in Western Springs and have two adult children. In his free time, Matt enjoys spending time with family and friends on Delavan Lake in Wisconsin and coaching youth basketball. "Hope is a special place to me," Matt said. "My first involvement was with the school's EYE program in 2021 as a student mentor. Since then, Hope's students and mission have been sources of inspiration to my entire family. One recent highlight was merging my work community with the Hope community for a day of introducing 40 students to the world of private credit. The students livened up our office and reminded my colleagues and me that our professional experiences are gifts to steward well. I'm very blessed to be a part of this community and couldn't be more excited about Hope's future." In its third decade as an organization, Matt's strategic thinking and dynamic leadership will be an asset as Chicagohopeacademy expand Hope's initiatives.
Guggenheim Investments has closed its Guggenheim Private Debt Fund IV at approximately $8.4 billion of total available capital, exceeding its initial fundraise target and hard cap. The final close marks the firm's largest dedicated private debt vehicle to date. The fund focuses on first lien senior secured loans in sponsor-backed and non-sponsor-backed middle market companies. Guggenheim serves as lead investor on over 90% of PDF IV's invested capital and sole investor on 35%, reflecting its conviction-driven approach. Investors are currently 50% called against commitments. The fund builds on Guggenheim's 20-year track record in private debt, having invested over $33 billion across more than 550 borrowers since 2002. The round was led by Ribbit Capital, with participation from Sequoia and Kleiner Perkins.
Kalamata Capital Group, a provider of financing solutions to small and medium-sized businesses, has closed a $111.87 million securitization through KCG Securitization II, LLC, Series 2026-1. The transaction is backed by a diversified pool of small-business receivables, including merchant cash advances and loans originated through Kalamata's platform. The securitization refinances the company's prior Series 2024-1 transaction. The Class A Notes received an A- rating, an improvement from the BBB rating in the previous securitisation. Proceeds were used primarily to refinance existing debt and support continued funding of eligible receivables. Founded by Steven Mandis, Kalamata provides online financing options of up to $500,000 to small businesses. Guggenheim Securities served as structuring adviser and initial purchaser for the transaction.