San Diego, CA
Aaron Cannata
Enterprise Account Executive
I build pipeline from zero, close complex enterprise deals, and translate business value into numbers a CFO will sign.
$1M+
Annual Quota
18-Month
Enterprise Cycles Closed
$0 to $1.5M
ARR Company Built and Sold
15+
Years in Sales
What I Do
Two sides of the same motion
Enterprise Sales (Hunter)
- Net-new logo acquisition through self-sourced outbound.
- Full-cycle ownership from first touch through procurement and legal.
- Multi-threading C-suite, Finance, HR, and technical stakeholders.
- Methodologies: Challenger, Miller-Heiman, SPIN, MEDDPICC.
Value Engineering and Enablement
- ROI models and CFO-ready business cases that clear Finance and Procurement.
- Built a Bureau of Labor Statistics-driven ROI calculator used to close enterprise logos.
- Authored outbound playbooks adopted across sales teams.
- Builds internal tools and demos with AI-assisted, agentic coding.
Tools
Proof of Work
Interactive ROI models I designed and built. The same value-engineering I bring to enterprise deals.
SaaS Spend Model
Prices shelfware, redundant tooling, and renewal leakage from two inputs, then writes CFO, CIO, and Procurement briefs.
Open the live model →
Sales Productivity Model
Prices what rep turnover, empty seats, and ramp time cost a revenue plan, with briefs for the CRO, CFO, and RevOps.
Open the live model →
Signature Wins
Deals that tell the story
TSMC
18-month enterprise cycle, closed from greenfield
- Challenge
- Greenfield territory with zero inbound support. Six stakeholders across multiple functions and Legal at one of the most demanding enterprises in the world.
- Action
- I self-sourced the entry point, multi-threaded every function over an 18-month cycle, and carried the deal through procurement and legal myself.
- Result
- Closed one of the largest deals in company history.
Anduril Industries
Four-vendor RFP won from a cold start
- Challenge
- A four-vendor competitive RFP with no incumbent advantage and no existing relationship.
- Action
- I opened the account with self-sourced cold outreach, then went high and wide across the buying committee to shape the evaluation.
- Result
- Won the RFP through to selection.
BISSource Consulting Group
Built, scaled, and sold
- Challenge
- Build a financial advisory practice from nothing.
- Action
- Co-founded the firm and scaled it from $0 to $1.5M ARR with a five-person team.
- Result
- Exited via a seven-figure sale in 2019.
Experience
Where I have carried the number
Senior Account Executive, Enterprise | TOOTRiS
Feb 2024 to Present
- B2B workforce and benefits SaaS sold to HR, Total Rewards, Finance, and C-suite buyers. $50K to $150K ACV.
- $1M+ annual quota as a perennial top performer with consistent attainment. 27+ months tenure on a team averaging 6 months.
- Built a two-input financial ROI model on Bureau of Labor Statistics data that cleared Finance and Procurement.
Senior Sales Director | S2W Media
Oct 2022 to Apr 2023
- Recruited to lead a net-new B2B media and demand-generation growth initiative.
- Role eliminated in a company-wide reduction in force, followed by a planned family sabbatical abroad.
Growth Account Director | Spiceworks Ziff Davis
Apr 2021 to Oct 2022
- Martech/ABM platform with first- and third-party intent data sold to enterprise B2B marketing leaders.
- Consistent top performer multi-threading Marketing, Finance, and Procurement.
Sales Director | Slashdot Media
May 2019 to Apr 2021
- SourceForge demand-generation with Bombora intent data. Grew the customer base from under 20 to over 500 accounts.
- Authored the team's highest-converting outbound sequence, adopted as the standard greenfield playbook.
Earlier | BISSource Consulting Group and financial services
2009 to 2019
- Co-Founder, BISSource Consulting Group: built and sold, seven-figure exit in 2019.
- A decade in financial services at LPL Financial, MetLife, and Scottrade.
I Build With AI
A seller who ships
I shipped Renewd.io, a customer success platform built from scratch using AI-assisted, agentic coding.
I use AI daily across account research, discovery prep, and pipeline workflow. No hype: it is a tool, and I know how to work it.
Education
BA Economics
UC Santa Cruz
Toolkit