Work that speaks. With the receipts.

Breezeway

Sales leadership · Property-operations SaaS

Operating role — Head of Inside Sales, one of the first ten employees

Building the engine: zero to twelve reps, ARR doubled in sixteen months.

Situation

An early-stage property-operations platform with product, early customers, and no sales team, no outbound motion, and no playbook.

My role

Head of Inside Sales. Recruited, hired, onboarded, coached, and led a team of twelve inside sales reps while carrying my own quota the entire time.

What I did

• Built the outbound system end to end in HubSpot: sequences, scripts, activity standards, demo process, follow-up frameworks
• Set team KPIs and coaching rhythms; ran call reviews and deal strategy
• Operationalized Challenger and Sandler across the organization
• Owned weekly pipeline inspection and forecasting, reporting coverage and conversion to company leadership

Results

• ×ARR doubled in sixteen months during my tenure leading the team
• ×Average sales cycle fell from 65 days to 27
• ×Average deal size grew more than 200%

What it shows

The full zero-to-one commercial build — people, process, pipeline — by someone who sold alongside the team instead of managing from a dashboard.

Company-level results during my leadership tenure; the whole team earned them.

Seismic

First sales hire · Sales enablement SaaS

Operating role — first sales hire; later Director of Client Development

First seller in the door: $0 to $3M+ in cold-sourced revenue.

Situation

Day one, there was a product, a market thesis, and me. No playbook, no pipeline, no process. Seismic went on to become the category leader in sales enablement.

My role

First sales representative, then Director of Client Development as the team grew toward forty.

What I did

• Built pipeline from nothing through highly personalized outbound into strategic and Fortune 500 accounts
• Developed business cases for VP- and C-suite buyers
• Co-built the prospecting, qualification, and CRM processes the scaling team adopted
• Interviewed, trained, and directly managed five reps as the organization grew

Results

• ×$3M+ in personally cold-sourced recurring revenue
• ×Averaged ~175% of quota, year over year, for three years

What it shows

I've personally done the hardest job in SaaS — creating demand where none existed — and systematized it so others could repeat it.

I helped build pieces of the early revenue organization. Seismic's growth belongs to a lot of people.

Enterprise expansion

Enterprise selling · National media company

Operating role — enterprise account executive. Client anonymized.

From a small pilot to a strategic partnership, roughly 7× the initial contract.

Situation

A national media organization heading into a merger: two companies, two cultures, and a leadership team with zero appetite for new technology mid-integration. No buying signal existed.

My role

Enterprise account executive, working directly with the CMO and senior stakeholders across both organizations.

What I did

• Spent close to a year with their CMO before a dollar changed hands — learning both businesses, showing up with ideas instead of a pitch
• Started deliberately small: a three-month pilot scoped to prove value without betting the merger on it
• Over-delivered beyond the contract: integration planning, change management across the combined org, coaching rhythms with frontline managers so adoption stuck
• Built the expansion case before the customer asked for it

Results

• ×Grew the relationship roughly 7× from the initial pilot into a strategic, company-wide partnership

What it shows

Expansion revenue doesn't come from accounts raising their hands. It comes from knowing the customer's business well enough to build the case before they ask — a discipline, not a lucky deal.

Enterprise selling experience from an operating role, not a TC×2 engagement. Customer details withheld.

Smoov

Founder · Consumer fintech

My own company — Founder & CEO

Zero to a launched consumer fintech, and a different education entirely.

Situation

Couples manage money together badly, and the tools assumed one person owns the account. Smoov helps couples manage and split shared expenses.

My role

Founder & CEO. Vision, brand, positioning, go-to-market, early team, fundraising, partnerships, user acquisition.

What I did

• Took the company from concept to a launched product
• Built the brand, the positioning, and the launch
• Owned creator-led distribution, organic content, and paid-acquisition strategy and budgets
• Raised capital, built partnerships, hired the early team
• Separately: conceived, built, and launched 940 Saturdays — idea to live consumer app in thirty days

Results

• ×20M+ organic social views
• ×Thousands of app downloads and early revenue

What it shows

Founder empathy, earned. I've raised money, built product, bought media, and lost sleep over payroll. Advisory clients get someone who has sat in their chair, not just sold to it.

Studio & investors

• ScienceLos Angeles startup studio — Smoov was built in their six-month program
• Spark CapitalInvested in Smoov through Spark's scout program

Founder-reported figures. Science and Spark Capital are Smoov's studio partner and investor — context for the founder experience, not TC×2 clients or endorsers.

Drift

Partner sales · Conversational marketing SaaS

Operating role — Partner Sales Manager, joined at ~90 employees

Leveraged revenue: a book of fifty-plus agency partners.

Situation

Mid-hypergrowth, with a partner ecosystem that could source and influence serious pipeline if someone made the partners good at selling the product.

My role

Partner Sales Manager owning a portfolio of 50+ marketing agency partners.

What I did

• Trained partners on positioning, discovery, and selling methodology
• Co-sold partners' biggest deals and ran strategic opportunities through the full cycle
• Managed partner performance against monthly revenue targets

Results

• ×~115% of quota over the trailing twelve months

What it shows

Fluency in channel and partnership revenue — the kind that comes from making other people successful at selling your product.

Mindtickle & Highspot

Enterprise account executive · Sales enablement SaaS

Operating roles — I still carry a bag

Then I went back onto the field to prove the methods still work.

Situation

Consultants rarely do this. After founding a company and advising six more, I went back into an enterprise seat — in one of the most competitive categories in SaaS — to keep the methods current.

My role

Commercial and enterprise account executive, managing a portfolio of 50+ customer accounts for expansion, renewals, and new business.

What I did

• Closed the fastest first deal in Mindtickle's history: forty days from start date to signature
• Finished at ~105% of quota at Mindtickle while informally coaching peers
• Hit 100% of annual quota in year one at Highspot; $1.3M+ in self-sourced closed-won total contract value
• Navigated complex, multi-stakeholder enterprise cycles into seven-figure deal environments
• AI-native daily workflow: conversation intelligence, AI prospecting and enrichment, LLMs for research, personalization, and deal prep

What it shows

The advice is current. Every playbook I build is one I'm still running.

My employer doesn't sponsor or endorse TC×2. TC×2 is an independent, part-time practice.