B2B Sales Consulting · Velocity Motions
SAILS Advisory is an 8-week sales consulting engagement for B2B SaaS founders running velocity motions: short cycles, $2K to $24K ACVs, BDR/AE economics.
Most sales consultants are enterprise operators trying to bolt MEDDIC onto velocity motions. It doesn't work. Velocity sales has its own physics, and most consultants don't know how to build for it. I do.
01 · The Problem
Velocity sales is a B2B motion built around short cycles, transactional buyers, and high-volume rep activity. ACVs run $2,000 to $24,000. Deal cycles close inside 90 days, often under 14. Reps work as BDR/AE pairs or full-cycle inside sales, and the team's job is to move volume through a documented playbook. It's the opposite of enterprise sales, where six-figure ACVs and 12-month cycles reward MEDDIC, multi-threading, and committee navigation.
You're closing deals, but it's still the founder doing it, or one rep out of three is carrying the number. Every deal still feels like the first one. There's no process to hand anyone.
Or you have a team in place, some results, but you can't explain why two reps are hitting and two aren't. Coaching is happening, but it's really just pipeline inspection.
The problem isn't effort. It's that velocity sales has its own physics. Short cycles, transactional buyers, BDR/AE economics, and nobody built you an engine that matches how your buyers actually buy.
| Dimension | Velocity | Enterprise |
|---|---|---|
| ACV | $2K to $24K | $100K to $1M+ |
| Sales cycle | Under 90 days, often under 14 | 6 to 18 months |
| Decision-makers | 1 to 2 | 5 to 12 (committee) |
| Rep motion | BDR/AE or full-cycle inside | Strategic AE, multi-threaded |
| Best-fit framework | Playbook, scripts, rep activity | MEDDIC, MEDDPICC, Force Management |
| What wins deals | Speed, message-market fit, volume | Relationship depth, political access |
02 · The Engagement
Before you can Always Be Closing, you need to Assess, Build, Coach.
Two tracks · One engine
Build track
For founder-led teams with wins but no system. You've closed deals, but the process lives in your head. We extract it, document it, and make it teachable before your first AE hire.
Scale track
For teams with reps in seat but uneven results. Some are hitting, some aren't. We diagnose the funnel, the rep distribution, and the coaching cadence, then rebuild what isn't working.
Assess
Weeks 1–2 · Track-specific
Build track gets a GTM Foundations Brief (ICP, positioning, motion fit). Scale track gets an Audit Report with 3 to 5 prioritized quick wins. No assumptions. No generic frameworks applied before we know what's actually broken.
Build
Weeks 3–6
A 20–30 page Sales Playbook built for your motion, including:
Coach
Weeks 5–8
Bi-weekly sessions during and after the Build phase, so nothing sits in a doc. Async support between sessions for quick reviews and gut-checks.
This is an async-first engagement. Most of the work happens between sessions, not in meetings. You get a founder with 8 years of operator experience, not a slide deck and a handoff.
03 · Who It's For
04 · About Matt
I've spent 8+ years scaling sales at a high-growth B2B SaaS company. Joined as an early sales hire and grew into VP of Sales, managing a team of 30+ reps across BDR, AE, and account management. I built the outbound SMB motion from scratch, scaled AE demos from ~100/year in 2018 to 10,000+/year by 2023, and helped grow ARR 6x over five years.
I authored the AE Playbook: the repeatable framework that standardized how the team discovers, demos, and closes across segments. I launched a new financial institution vertical from zero and engineered a 5x increase in average deal size in under 24 months.
SAILS is built on what actually worked, not what looks good in a deck.
8+
years scaling B2B SaaS sales
30+
reps managed as VP of Sales
6×
ARR growth in 5 years
100 → 10K+
AE demos per year
5×
avg deal size in 24 months
05 · Investment
Fixed-price · Scope-bound · 8 weeks
Sized to your stage, not your sticker price.
Every SAILS engagement is fixed-price and scope-bound. The investment is shared during the discovery conversation, scoped to the right track for where you are: Build (no system yet) or Scale (team in place, uneven results). Founding cohort rates available for the first few clients.
Get a Custom ProposalFixed-price means fixed. No hourly overages, no scope creep billing. If you want continued support after week 8, a coaching retainer is available starting at $2K/month.
06 · FAQ
Build track is for teams with wins but no system: typically founder-led sales that needs to be handed off. Scale track is for teams with reps in place but uneven results. We determine which fits during the discovery call.
No. Many Build track clients are pre-first-hire. We build the engine before you hire into it.
The engagement is designed to be async-first. You'll need to complete a diagnostic questionnaire before kickoff and commit to bi-weekly 60-minute sessions during the Coach phase. Outside of that, the work is mine.
Coaching retainers are available starting at $2K/month for continued bi-weekly sessions and async support. No obligation. It's an option, not the default.
Possibly. The frameworks are built around B2B SaaS velocity motions, but the underlying physics apply to any short-cycle, transactional B2B sale. Reach out and we'll be direct about fit.
07 · Get in Touch
The first step is a 30-minute discovery call. No pitch, no deck. Just an honest conversation about where you are and whether SAILS is the right fit.
Or email directly: matt@sailsadvisory.com
Prefer to write? Tell me what's broken and I'll come back to you within one business day.
