Real frontline expertise
“Unlike many enablement professionals who lack frontline selling experience, Chad brings real-world sales expertise to the table.”
AK
Alex Kravitz
Account Manager, NetDocuments
Live question, 1 of 20
There is a deal you lost that you still cannot explain.
In how many of your last five deals did you check that your contact could get budget approved?
None
All 5
Chad Rawlings. Helped scale Outreach and InsideSales past $100M.
Two different problems
Which one are you?
You carry a number
I am an individual seller
AE, SDR, BDR, or anyone with a quota.
You are working hard and the number is not moving. You have a development plan with twenty things on it, and you know you will not do any of them.
Score yourself. Free.Six minutes · No credit card
You carry a team
I run a team or a company
VP of Sales, CRO, founder, or RevOps lead.
You know something is leaking. You cannot tell whether it is a skill problem, a process problem, or a people problem, and the forecast is not holding.
Score your team. Free.Two minutes · No credit card
The AI paradox
Your buyers are avoiding your reps.
73%
of B2B buyers actively avoid suppliers who send irrelevant outreach.
Source: Gartner, survey of 632 B2B buyers, published June 2025.
Teams added AI to reach more buyers. Buyers answered by screening sellers out. The teams winning now use AI for the work buyers never see, and put a human in every moment that decides the deal.
3.7 times more likely to meet quota
Sellers who effectively partner with AI tools are 3.7 times more likely to meet quota.
Source: Gartner, survey of 1,026 B2B sellers, September 2024.
If you want the researchWhy more AI is producing fewer deals, and what to do instead. Read The AI Paradox →Illustrative, no numeric scale
Outreach sent
Buyers who engage
In their words
The people who worked with Chad.
3X
Rocketlane grew 3X year over year.
Source: Rocketlane
Results vary by company and team.
Measurable improvements in my meeting rates
“Since working with Chad, my performance has skyrocketed. I've seen measurable improvements in my meeting rates and confidence in prospect conversations.”
MH
Max Holman
Account Executive, Canals
Worked with Chad at Rocketlane
Transformational for Rocketlane's sales
“Chad's contributions have been transformational for Rocketlane's sales and business development efforts the past two years. His expertise from initial discovery to demo, business case creation, and deal assessment has helped us level up, resulting in strong growth across our teams with his training and coaching.”
SG
Srikrishnan Ganesan
Co-Founder & CEO, Rocketlane
One of the largest deals in company history
“...closed one of, if not the largest deal we had as a company in FY 2019.”
BB
Brooke Bachesta
GTM Enablement - Onboarding
Worked with Chad at Outreach.io
I'd hate to sell against him
“Chad is an awesome teammate, an asset to any sales org fortunate enough to have him, and personally, I'd absolutely hate to have to sell against him.”
CD
Chris Dankowski
Sr. Sales & AI Innovation Strategist., Salesloft
Worked with Chad at Outreach
A force multiplier
“He's a force multiplier who will make your whole team stronger.”
DB
Dave Breshears
Founder, Silicon Hills Revenue Lab
The best I've seen at uncovering pain
“He's the best I've seen at uncovering pain and compelling events during discoveries and uses the cost of inaction to move the deal forward.”
RC
R. Craig Johnson
Chief Sales Officer (CSO), Opiniion Inc.
Forecast and deliver, month after month
“Not only does he have a flawless sales methodology but he has the performance to back it up. Month after month Chad would forecast and deliver sales results and revenue all while delivering a customer experience that is unparalleled.”
CM
Chad Medeiros
Middle Enterprise Account Executive, Proofpoint
Worked with Chad at InsideSales.com
What you get
Not a description of the report. The report.
A real report layout, with the skill names held back until the report is yours.
Find your twoYour two · Skills Report
Your two, named here
Skill 07, unlocked in your report1
Skill 12, unlocked in your report1
Skill 04, unlocked in your report3
Skill 16, unlocked in your report5
Wiring and behavior
Your pattern and your practice agree.
Who this is for
You have already tried the standard fixes. They did not produce what you expected.
That is specifically what we build for.
You added reps but quota attainment stayed flat.
You bought a training program and the methodology did not outlast the quarter.
You implemented a new CRM and pipeline hygiene improved but the win rate did not.
You ran a team offsite and everyone was aligned for two weeks.
You are not looking for another program. You want a diagnosis and a system.
You want the system built, not just described.
Who is telling you this
Chad B Rawlings
Twenty years carrying a bag and running the teams that carry them. Part of the sales organizations that helped Outreach.io shape product and drove sales, and InsideSales.com grow, past a hundred million each in recurring revenue. President’s Club at every company.
None of that is why you should listen. This is. I spent a year losing deals I should have won because I could not bring myself to ask a buyer to commit, and I had convinced myself that was decency rather than fear.
My father saw it before I had made a single sale. It took me twelve months and one deal I badly needed to catch up to him. Everything here exists to find that thing in you faster than I found it in me.
More about the work$3M → $100MHelped Outreach.io, shape product and drove sales including the first seven-figure enterprise deal
$7M → $110MHelped InsideSales.com grow sales and team leader
Every orgPresident’s Club, twenty-year career
We are gathering verified client outcomes from PiVOTSALES engagements now. Every future case study will be a real, attributed, specific result.
The whole method, in writing.Every framework, every number named and dated, including the statistics he refused to use. The AI Sales Method →Where this goes
The assessment is free. Here is everything it can lead to, and what each one costs.
Nothing here is a surprise later. Most people stop at the first two, and that is a fine place to stop.
- You are hereThe assessmentFreeTwenty skills scored from what you did in your last five deals. Your two costliest, named.
- 01The full report$47The full diagnosis of your two costliest gaps: the cost pattern, the evidence, and a reflection for each.
- 02The AI Sales Method$12.99 presaleThe whole method in writing. Every number named, dated, and checkable.
- 03Quota Mastery$997A hundred and twenty days live, then a year of access. Founding rate for the first twenty-five.
- 04Revenue Evaluation$9,999Ninety minutes on your numbers. A scored diagnostic, a cost of inaction figure, a thirty sixty ninety plan.
- 05The GTM BuildCustom bidWe install the system. Methodology, workflows, tooling, coaching, handed over running.
Leading a team and already know you want to talk?Skip ahead to the Revenue Evaluation
You already know something is broken. The question is specifically what, why, and what it is costing you every month you leave it in place.
START.Six minutes · Free · No credit card