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**Transaction Advisory AI Lead | Dobs AI - ** San Francisco AI startup automating financial due diligence and quality of earnings — the work at the heart of every M&A transaction. Our AI agents handle data room ingestion, EBITDA normalization, working capital analysis, customer and revenue diligence, pro-forma adjustments, and report drafting.
ABOUT THE ROLE We are hiring our Transaction Advisory AI Lead, a senior practitioner from a Big Four or Tier 1 advisory firm who will own the methodology behind our AI agents, run live engagements with our partner CPA firms, and turn the patterns from real deals into product. You are the most senior transaction advisory voice inside Dobs and the practitioner who teaches our AI how to do this work at scale. This is a hybrid role: part subject-matter expert, part product owner, part deal practitioner.
You will: Own transaction advisory methodology end-to-end. Define how Dobs AI runs working capital analysis, EBITDA normalization, debt-like items, customer and revenue diligence, pro-forma adjustments, and proof-of-cash. You set the standard our AI agents work to. Lead live engagements with partner CPA firms. Be able to take a sell-side or buy-side QoE engagement from kick-off to deliverable: scoping, data room review, financial diligence, drafting, and presenting findings to buyers, sellers, and their advisors. Turn deal patterns into product. Sit with our partner firms and PE / strategic clients, gather what they actually need from an AI-augmented practice, and work directly with our engineering team to ship it. You are the voice of the practitioner inside the product. Improve the AI system. Review agent outputs on live engagements, identify where the model is wrong or weak, and fix it through prompt iteration, methodology refinement, knowledge-base updates, and direct collaboration with engineers. You will be expected to be comfortable enough with AI tools and lightweight code to debug, iterate, and ship improvements yourself. Be the trusted senior voice on deals. When a partner firm has a hard call on a working capital adjustment, a customer concentration question, or a contentious EBITDA add-back, you are the person who weighs in. Build the firm-wide knowledge layer. Codify playbooks, adjustment libraries, industry-specific patterns, and review checklists that scale across the firm and across deals.
ABOUT YOU This role is for an experienced transaction advisory / QoE practitioner who is excited to stop billing hours and start building leverage on top of their craft. You are senior enough to be the most knowledgeable person in the room on financial diligence, and curious enough to want to understand how AI is going to reshape this work — because you will be the one shaping it. You have: 5–10+ years in Transaction Advisory Services (TAS), Quality of Earnings, or Financial Due Diligence, ideally at a Big Four firm (Deloitte, EY, KPMG, PwC) or a Tier 1 advisory practice (Grant Thornton, BDO, RSM, Alvarez & Marsal, FTI, Houlihan Lokey, or equivalent). Manager-level or above in the practice (Senior Manager / Director / Partner-track ideal). You have personally led engagements, not just supported them. Hands-on full-cycle deal experience: net working capital analysis, debt-like items, EBITDA normalization, revenue and customer analysis, cash-to-accrual, pro-forma adjustments, and report drafting that holds up under buyer scrutiny. Comfort with AI tooling and lightweight technical work.
You are not afraid of touching prompts, reviewing AI output line-by-line, working with APIs, or sitting next to an engineer in a Git-tracked repo. You don't need to write production code, but you should be able to iterate alongside an engineer and reason about the system. Sharp communication. You can explain a working capital adjustment to a CFO and a model output quirk to an engineer in the same hour, in clean English. CPA, CFA, ACA, ACCA, or equivalent qualification preferred. Strong written and spoken English (C1+) is required.
Full-time, remote.
CONTACT lena@dobs.ai
from 5 years
Experience
Full-time
Employment
Remote
Work Format
Lead
Grade
C1 - Advanced
English Level
Finance
Specialization
AI
Industry
Startup
Company Type
By job title
C1 - Advanced
English Level
Finance
Specialization
AI
Industry
Startup
Company Type