Insights on AI in GTM and the future of enterprise sales.
Essential personal finance strategies specifically tailored for software sales professionals with variable commission income.
A concrete budgeting framework for variable commission income: what expenses should never depend on commission, and how to separate fixed vs variable lifestyle.
A cooling-off framework for windfalls: taxes first, buffers second, investing last, and spending intentionally — not reflexively.
A candid look at the traps: lifestyle inflation after good years, ignoring taxes, overconfidence during hot streaks, and underpreparing for down cycles.
How personal finances affect performance: negotiating power, risk-taking, quota pressure, and why financial stability improves selling quality.
Connecting burnout to money: lost earning years, bad financial decisions under stress, and how financial runway affects risk tolerance at work.
Replacing generic savings advice with comp-aware guidance: savings targets based on volatility, emergency funds sized for drawdowns, and how strategy changes at different career stages.
Understanding how commission checks are taxed, what gets withheld, and how to avoid surprises at tax time.
A first-principles system for handling variable commission income: smoothing cash flow, separating base vs commission, and funding lifestyle decisions.
Financial shifts across career stages: IC to manager to exec, variable comp to leverage to equity, and when to de-risk vs invest in optionality.
Demystifying mixed compensation: base, commission, accelerators, RSUs vs cash timing, and tax implications salespeople often miss.
Portfolio construction through the lens of income volatility: when your job is already risky, concentration risk, and why stability elsewhere matters more.
Practical strategies for building a side business while working as an Account Executive, without burning out or violating employment agreements.
A comprehensive breakdown of Account Executive OTE by segment, quota-to-OTE ratios, and what to expect at each level.
Rethinking emergency funds for variable income: why 3-6 months is insufficient, tying fund size to sales cycle length, and planning for missed quarters.
Risk management for sales professionals: why disability insurance, life insurance, and downside protection matter more when income is volatile.
A comprehensive guide to Solo 401(k)s for software sales professionals: who qualifies, contribution limits, tax advantages, and when it makes sense.
Understanding how quota-to-OTE ratios affect your earnings potential, risk, and financial planning.
A practical framework for handling large commission checks — from taxes to investing to avoiding costly mistakes.
