How should a newly hired senior sales leader spend their first months, and what should the company do for them?

Kieran Flanagan · Aug 10, 2022

Good onboarding means a 100-day plan whose goal is that the hire understands their role, their team and the path to success — not that they have achieved specific deliverables

New joiners arrive not knowing what to do, so the plan schedules the people they should meet and checks in every two weeks to make sure they feel set up for success

Scope: there are still things you want them to do along the way

45:15 20 Growth: Why You Need a Growth Hire Pre Product-Market-Fit? Why Every Company Will Be a Media Company and How To Do It | Communities; What Really Are They? How To Build Them? What Makes The Best? Why Do Many Not Work? | Kieran Flanagan, SVP Marketing @

Unknown · Nov 16, 2022

Leadership hires should be freed from having to deliver anything in their first month and instead spend it learning the product and building relationships — starting with the people they'll need a year from now, like engineering and product leaders, before their own sales team.

You hire a leader for the next five years, not six months, and if you miss the chance to build those personal connections early it's very hard to do once you're six months into the role.

Scope: applies to leadership hires

Kevin Egan · Jul 12, 2023

A sales leader joining a new company should avoid pattern matching from their previous company and instead invest time in their peer group, especially engineering leadership, to understand how the product solves problems

Every environment is different

32:27 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Chad Peets · Aug 23, 2024

A first-time sales leader's first priority should be learning the business as fast as possible — getting in front of customers and talking to salespeople — before trying to lead

People now report to you expecting you to add value, and you can't add value to reps until you understand the business

58:36 20Sales: How Snowflake Built a Sales Machine | Why You Have to Hire a CRO Pre-Product | Why Most Sales Reps Do Not Perform | Why Hiring Panels are BS in Interviews | Why Remote Sales Reps Do Not Care About Their Development with Chad Peets

Rich Liu · Jun 7, 2023

A sales leader starting a new role should immediately align with the CEO on the most important things to accomplish this quarter and the one or two metrics that prove it's working

46:28 20Sales: PLG and Early Adopter Sales are Gone, How to do Sales Forecasting in 2023, Why You Cannot Do PLG and Enterprise from Day 1 at the Same Time and Which is Easier to Start, How to Onboard, Manage and Scale Reps with Rich Liu, CRO @ Everlaw

Lori Jimenez · Aug 2, 2023

The biggest mistake founders make when hiring sales teams is failing to set mutual expectations with the sales leader

If the founder believes one growth number and the first sales leader believes another because expectations were never set, you get a mismatch

47:37 20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

Dan Fougere · Nov 22, 2024

A new sales leader should map out specific wins for week one, month one, 90 days, six months and one year, agree them with the CEO as realistic, and then do only those things

Getting visible wins on the board — game-changing hires, game-changing deals, instrumenting the business, messaging, efficiency, productivity — is what establishes the leader

66:54 20Sales: What I Learned Scaling Datadog from $60M to $1BN in ARR | How to do Outbound in 2024 | Why Discounting is Dangerous and Contract Sizes are Misleading with Dan Fougere

Lauren Schwartz · Oct 19, 2022

For a sales leader starting a new role, nothing is more important than listening to customers.

42:37 20 Sales: How To Structure The Interview Process for All Sales Reps, The Must-Ask Questions When Identifying Potential Sales Talent & The 3 Biggest Mistakes Founders Make When Hiring Their First Reps with Lauren Schwartz, VP of Enterprise Sales @ Fivetran

Unknown · Nov 16, 2022

A new sales leader who spends their first two months in conference rooms without talking to at least one new customer every week is a major red flag about their customer orientation and the org they will build.

A leader's point of view on the year's one or two priorities has to come from hearing customers directly as well as from the founder.

Scope: first two months

Matt Rosenberg · Oct 4, 2023

Founders' claims that product-market fit is figured out and the product will sell itself are never true when a sales leader arrives

The company rests on the incoming sales leader's shoulders precisely because nothing has actually been figured out

8:24 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly

Ben Fiechtner · Aug 2, 2024

CROs and heads of sales fail in new roles because they copy-paste the playbook from their last company instead of bringing design principles and listening to the specific company's needs

Every company has different challenges and sits at a different point in its maturity journey, so the old playbook doesn't transfer

49:57 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Lori Jimenez · Aug 2, 2023

A new sales leader should learn deeply in their first 90 days but expect to relearn everything in the following 90 days

The first period builds a foundation of context, but you then pivot your mindset and build off it — learning doesn't stop after quarter one

48:02 Expect to relearn after the first 90 days

Doug Adamic · Sep 8, 2023

A new sales leader's first job is to understand what buying criteria must change in prospects' minds so those criteria uniquely lead to their product

Without knowing how to shift buying criteria toward your product, you aren't setting yourself or your team up for success

48:48 Start by defining the buying criteria to shift

Unknown · Nov 16, 2022

The CEO should actively engineer the new leader's onboarding — making the introductions to peers and board members, spending hours walking them through the product — rather than dropping them in to see if they figure it out.

Testing should have happened in the interview; once they've joined, making them successful is a mutual job, and heavy investment in the first months pays back over the next several years.

Unknown · Nov 16, 2022

Early rejection of a new leader by the existing team is a key warning sign, and the CEO should proactively poll every team member on the value the new hire is delivering — but such rejection is usually about the hire's approach rather than their quality and can often be resolved.

He has seen cases where a hire got significant rejection after three months, and once it was talked through with the team the person became much loved.

AJ Tennant · Oct 23, 2024

A new head of sales at a Series A company should personally get hands dirty running deals, and should orient around the three Ps: product, people, position

Learning and selling the product, building internal relationships, and understanding your position is the same framework he uses for career decisions and for coaching AEs

50:57 Orient around product people position while personally running deals

Shaunt Voskanian · Mar 21, 2026 · hedged

He spent too long observing and understanding the existing culture when he joined Figma, and would move to implement changes somewhat faster if doing it again

He over-corrected against being the new leader who comes in hot and changes things he doesn't yet understand

56:35 Err toward changing faster than observing longer

Chad Peets · Jan 9, 2026

A new sales leader who hasn't immediately started consistent, frequent one-on-ones with their direct reports is a red flag

cadence with directs reveals whether they are actually working to understand the business and their people

63:04 One on one cadence with directs is the first signal

Matt Rosenberg · Oct 4, 2023

A new sales leader should ask the same rubric of ~20 questions to every person and function in the business

Repetition speeds the rate of learning and produces pattern recognition, letting you map organizational strengths and weaknesses in thirty days that would otherwise take six to nine months

46:22 Same question rubric across the whole org