Does remote work hinder how sales teams learn and develop?

Matt Rosenberg · Oct 4, 2023

Early sales learning is harder in a remote setting

The level of conversation among peers is simply different when remote

23:29 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

Ashley Kelly · Jun 7, 2024

In-office SDRs perform much better than remote ones, especially for outbound

Sitting next to each other lets reps shadow screens, see where others click, and hear calls on the floor — learnings you can't get remotely

Scope: especially for outbound; she herself works remotely from Dallas and travels monthly

46:27 20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

Chad Peets · Aug 23, 2024

Inside sales reps get better faster by being in the office, and a rep unwilling to make a 30-minute commute to advance their own career is not worth hiring

Being in the office accelerates development; refusing a small sacrifice for your own career shows you don't care enough to be exceptional

Scope: specific to inside sales reps

0:00 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

Harry Stebbings · Aug 23, 2024

Physical colocation creates real information advantages beyond the filtering argument — overhearing product, support and customer conversations builds a better cross-functional organization

You passively absorb what product is building and what problems support is hearing, which makes the organization work together better

45:55 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

Carlos Delatorre · Jan 24, 2025

Sales teams are much more productive in person than remote.

Reps learn faster and morale is higher — a colleague having a good day pulls you through your bad day — and managers can observe and course-correct mistakes reps don't know they're making.

Scope: specific to sales teams

57:12 20Sales: Why Every Sales Rep Should Do Pipeline Generation & How to Teach Them | Verticalised Sales Playbooks: When and How | How the Best Sales Reps and Leaders Structure Their Time with Carlos Delatorre, CRO @ Harness

Kyle Norton · May 30, 2025

Early-career SDRs and BDRs should be in the office five days a week; co-location produces a sizable performance impact

The newest fully in-person SDRs and BDR all broke first-month EMRR-sourced records and month two and three reps beat previous records, which he attributes to sitting next to each other and their managers

Scope: evidence is recent cohorts at Owner; applies to SDR/BDR roles, not engineering

20:09 20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best Sales Reps with Kyle Norton, CRO @ Owner

Harry Stebbings · Jun 27, 2025

Remote work is bad for sales and product organizations because it destroys the ambient knowledge transfer you get from overhearing colleagues' calls and customer support

Hearing a rep repeat messaging that works lets others copy it, and sitting near support surfaces recurring customer complaints early

47:54 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

Harry Stebbings · Feb 14, 2026

Salespeople gain multifunctional benefits from time in the office — overhearing peers' messaging that works and learning from other functions like support about recurring customer problems — though they also need to be out with customers

You learn from hearing a colleague's message land, and from hearing support discuss recurring customer challenges you can name as core problems you solve

Scope: concedes reps also need to be with customers; calls it a nuanced thing

38:59 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Shaunt Voskanian · Mar 21, 2026

Onboarding should return to in-person, classroom-style delivery with internal thought leaders, rather than the remote formats adopted during COVID

They got away from it during COVID and are deliberately going back; the content spans ecosystem education, positioning, best customers, product and the full sales process

Scope: Figma is mid-rollout — soft launch of the new version just happened

39:11 20Sales: Inside Figma's $1BN ARR Revenue Machine | Why We Do Not Have Customer Success or SDRs | Why I Do Not Believe in Sales Quotas with Shaunt Voskanian, CRO @ Figma

Becca Lindquist · May 2, 2026

Sales teams get significantly more out of working in person, and she personally goes to the office five days a week

You get much more from working in person with your team; she gets FOMO when not in the office

63:24 20VC: Inside Clay's Sales Playbook Scaling to $100M ARR | How to Set Sales Comp Plans | How to Read Sales Talent Linkedin Profiles | What Profiles to Hire & Fire | How to Increase Performance and Speed in Sales Teams with Becca Lindquist

Julian Teixeira · Mar 7, 2025

Remote sales teams work, but in-person gatherings remain essential and worth investing in annually

Within 15 minutes in person you can tell who's engaged, who's in it, and who's full of it

Scope: he leads a remote sales team himself

44:35 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Julian Teixeira · Mar 7, 2025

Remote leadership costs far more energy because you must actively go seek what's happening instead of simply seeing it in the room

Being physically present surfaces team signals passively; remote requires deliberate effort

Scope: he mitigates it with end-of-month/quarter gatherings of a subset of the team and centers of excellence

45:33 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Kim Graves · Jun 27, 2025 · hedged

You cannot build the same kind of collaborative, dedicated sales team with everyone working from home; the best sales teams treat celebration and collaboration as a competitive advantage

There is something irreplaceable about in-person collaboration

Scope: she advocates hybrid, at least three days a week in office, not full-time in office

48:20 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

John McMahon · Nov 28, 2025

Sales should stay a hybrid of remote and in-person: remote genuinely opens access to senior buyers, but reading a room in person is how reps build and calibrate intuition, which remote work costs them

In-person he can walk a room and label gatekeepers, champions and enemies, then test those reads against how the meeting unfolds, constantly adjusting his gut; that feedback loop is very hard over Zoom

Scope: remote access to senior people is a real benefit he didn't think possible years ago

61:07 20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

David Vélez · Sep 11, 2023 · hedged

Hybrid work is the right model for Nubank even though full in-office would improve decision speed and innovation, because a mandatory-office policy would cost access to critical global talent

Being based in Latin America means the talent Nubank needs is in Berlin and San Francisco, not Sao Paulo or Mexico City, so its situation differs from a typical Silicon Valley company

Scope: he is still making up his mind; minimum of one office week every six to eight weeks; specific to Nubank's Latin American footprint; still tracking efficiency, productivity and engagement metrics

58:04 20VC: Lessons Building Nubank to the Largest Neobank in the World, How AI Changes The Future of Finance, Leadership Lessons from Sequoia's Doug Leone & What European and US Fintech Can Learn From LATAM with David Velez, Founder @ Nubank

Matt Plank · Dec 20, 2024

Companies have lost something real in culture by not being fully in-office; if he could keep his current people and force them into an office he would do it in a heartbeat

He misses the vibe of everyone being in on the same days and believes the office company culture has degraded

Scope: acknowledges remote hiring gives access to better talent; Rippling already requires three days a week for anyone near an office; remote hires are still part of the culture

65:07 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank

Shaunt Voskanian · Mar 21, 2026

Remote sales teams are not dead, though fully remote setups are harder and put much more pressure on leadership; going fully in-office costs you access to real talent

Talented people have moved to other cities and started families and won't relocate, so an office-only policy excludes them

Scope: fully remote is harder and pressures the system; requires more of leadership

56:01 20Sales: Inside Figma's $1BN ARR Revenue Machine | Why We Do Not Have Customer Success or SDRs | Why I Do Not Believe in Sales Quotas with Shaunt Voskanian, CRO @ Figma

Vlad Tenev · Jul 14, 2025

In-person work is materially better; Robinhood has operated much better since reversing its remote-first policy

Bringing people back into the office allowed better onboarding and operation

Scope: the reversal was painful and angered many employees

40:24 20VC: Vlad Tenev on Robinhood's $85BN Resurgence | Tokenizing SpaceX & OpenAI | Building Nine Revenue Lines Over $100M | Why Crypto Will Be Robinhood's Biggest Revenue Line | Why Stablecoins Will Replace Banking Rails

Jesse Zhang · Sep 19, 2025

In-person work is way more productive than remote

In-person communication lets ideas flow much faster, as he and his cofounder experience directly, versus his prior remote company during COVID

Scope: remote has pros and cons; says it ultimately comes down to founder personality

32:40 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon

Linda Lian · Apr 1, 2021

A fully remote, fast-moving early startup should hire experienced people rather than junior ones, because juniors learn largely by osmosis and remote work removes that.

Early-career learning comes from being a fly on the wall near senior conversations; putting an ambitious junior in an isolated room puts the onus of reaching out on them, which risks their success.

Scope: near-term plan only, roughly through the end of this year; specific to being a COVID-era, all-remote company

16:24 20VC: How To Deliver Feedback with Compassion and Clarity, WTF Are Values Really and How To Instill Them & Raising $50M+ From Index and Greylock but Remaining in Stealth for 12 Months with Linda Lian, Co-Founder & CEO @ CommonRoom

Carles Reina · Feb 14, 2026

Building a sales culture remotely requires being ruthless and hiring only autonomous, senior, high-energy people rather than juniors

Building sales is tough and building it remotely is even tougher, so you have to be constantly on top of it and people must be forced onto the road

Scope: applies to remote sales orgs

26:29 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Sam Blond · Apr 12, 2024 · hedged

A company started today should be built in person, including the sales organization; a mature business that has already gone remote can't realistically reverse it

Once remote, the genie is out of the bottle

Scope: states he is 'very biased'; distinguishes new startups from already-remote mature businesses

67:07 20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

Clay Bavor · Jul 4, 2026 · hedged

For a young company, building culture, shared norms and camaraderie remotely is very challenging, so in-person work is the right default.

Rituals only emerge in person, enterprise software is a team sport that feels different through Zoom squares, and apprenticeship and mentorship for younger employees depend on looking over experienced people's shoulders.

Scope: won't say remote culture-building is impossible; argument framed specifically for young companies

49:23 20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra

Harry Stebbings · May 2, 2026

Work-from-home Fridays should not be allowed — in Europe they have turned Friday and Monday into a de facto three-day weekend

Scope: framed as a European pattern

63:44 20VC: Inside Clay's Sales Playbook Scaling to $100M ARR | How to Set Sales Comp Plans | How to Read Sales Talent Linkedin Profiles | What Profiles to Hire & Fire | How to Increase Performance and Speed in Sales Teams with Becca Lindquist

Harry Stebbings · May 16, 2026

Work-from-home Fridays are a fiction — people who take them simply work four days a week and should admit they aren't working as hard.

44:43 20VC: Lessons from Jensen Huang on "Founder Mode" | How to Know if OpenAI or Anthropic Will Kill your Company | How USV Liking Music Made Them $1BN on an Investment | The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao @ Abridge

Varun Mohan · Jun 2, 2025 · hedged

Building a company remotely is harder and requires a much more principled organization, because in-person teams have an unfair speed advantage in aligning and pivoting

Getting engineers in the same room and on the same page within minutes gives flexibility that distributed time-zoned teams lack, and early-stage companies must pivot fast since their first ideas are wrong

Scope: harder rather than impossible; most acute in the early days when pivots are frequent

25:58 20VC: Windsurf Founder on Will Model Companies Own the App Layer | Why Moats Do Not Exist in a World of AI | Why the Notion of Single Person $BN Companies is BS | Lovable vs Bolt & Cursor vs Windsurf: How Does it All End with Varun Mohan

Shiv Rao · May 16, 2026

In this moment, more in-person time is unambiguously better — especially for engineering, product and design — even though Abridge runs three days in office as a concession to commutes.

Things are moving so quickly that co-location at whiteboards benefits nearly everyone in the company; the three-day setting is still being tuned because some people travel long distances.

Scope: Abridge is currently three days in office; still adjusting the sweet spot

44:59 20VC: Lessons from Jensen Huang on "Founder Mode" | How to Know if OpenAI or Anthropic Will Kill your Company | How USV Liking Music Made Them $1BN on an Investment | The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao @ Abridge

Jerry Murdock · Feb 28, 2026

Remote decision making is very difficult and remote management should be viewed with suspicion

Humans today need to be together; as the remote co-founder he had to commit to entrepreneurs on the spot while his team was elsewhere, which was hard on the team, whereas co-located teams can decide together easily

Scope: a function of the team, who's involved, and experience; unclear how this changes as autonomous agents replace humans

43:42 20VC: Why Cursor is Dead | An AI Tsunami is Coming & You Need to Prepare | Systems of Record Become Valueless Databases with Agents | Is This The End of Tech Private Equity with Jerry Murdock, Co-Founder of Insight Partners

Gokul Rajaram · Mar 16, 2026

Pure remote does not work for early-stage companies even with the right culture; teams need to be in person at least three days a week

He has seen companies die because remote founders couldn't align on strategy or move fast enough; iteration speed suffers massively under pure remote

Scope: doesn't need to be five days a week; specific to early-stage companies

69:41 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram

Ryan Petersen · Jun 20, 2026

Remote work is white collar fraud — with a three-year-old and five-year-old at home, the idea that he could do any work at his house is a total fantasy

He has a three- and five-year-old; the idea he could do any work at his house is a total fantasy

0:00 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport

Ryan Petersen · Jun 20, 2026

Remote work is 'white collar fraud' — meaningful work does not get done at home

With young children at home, even a private office with a closed door doesn't allow real work; kids come home at 3pm while the workday must continue

Scope: argued from his own experience with a three- and five-year-old

36:53 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport

Vlad Tenev · Jul 14, 2025

Robinhood ingested too many employees too fast during 2020-21 and that, combined with being fully remote, gummed up the company's ability to operate and ship

Revenue quadrupled to near $1B while remote during the pandemic; new hires didn't know how to work with the team, and customer support had to scale faster than the customer base in a pre-AI era

39:15 Over hiring during remote work gummed up operations

Vlad Tenev · Jul 14, 2025

Going remote-first is not a one-way door — the decision can be reversed, as Robinhood proved

Robinhood pulled back an entirely remote-first policy successfully

40:44 Remote first policies are reversible not a one way door

Sanjit Biswas · Dec 8, 2023

There is no one-size-fits-all office policy: tiny startups benefit enormously from being literally in the same room, but at a couple thousand people flexible work is the better choice

Co-location gives startups fast cycle time via overheard conversations, but at scale a single-location constraint forces you to lower the hiring bar

27:38 Co locate when tiny flex at scale to protect the hiring bar

Zaria Parvez · Jan 19, 2024

Duolingo's social content could not have been created as well fully remotely

The random quirkiness and physical objects of the workplace — the suit, props like using a water bottle as a microphone — are what sparked the content

15:17 In person workplace quirks are the source of creative output

Chad Peets · Aug 23, 2024

A company losing inside-sales candidates to remote-offering competitors is actually winning the recruiting battle, because the in-office requirement filters for reps who invest in their own careers

The requirement selects for people willing to make sacrifices to do something great, and a team built from those people will beat one built from the others

44:54 In office requirement is a useful candidate filter

Carles Reina · Feb 14, 2026

Best-practice sharing across a sales team does not require an office; distributed teams can share what works effectively over Slack

As the European team expanded it became extremely good at posting working tactics into Slack for others to copy

39:31 Distributed sharing over slack replaces the office

Frank Fillmann · Mar 22, 2023

Building new relationships remotely is very difficult, though retaining existing ones remotely is easier; something is missing from the cycle without face-to-face and it has to be recreated.

He observes the absence of in-person contact leaves a gap in the sales cycle as teams cycle back to face-to-face.

45:46 Remote hinders building new relationships but not retaining existing ones

Kyle Norton · May 30, 2025

Staff software engineers don't need to be in an office to do their job well, so a company can stay primarily remote while pulling specific roles back in

19:54 Senior engineers can remain remote while other roles return to office

Becca Lindquist · May 2, 2026

Office attendance should not be tracked — productive people earn location flexibility, but underperformers who aren't in the office should be confronted about it

Performance, not attendance, is the thing being managed

63:59 Flexibility earned by performance not tracked attendance

Ryan Petersen · Jun 20, 2026

The idea that work from home benefits highly paid employees is a fantasy — done correctly it should be a global labor arbitrage that benefits very smart, lower-cost workers abroad

Because purchasing power differs across countries, remote hiring should mean finding geniuses who cost far less, not a $250k-a-year employee in Jackson Hole skiing four hours a day

37:51 Remote is only justified as global labor arbitrage

Harry Stebbings · Jun 20, 2026

Zoom calls are not worth doing because interaction quality is low and participants disengage

He finds the quality of interaction poor and himself disengaged

39:15 Video calls are low quality disengaged interaction

Chad Peets · Jan 9, 2026

Inside sales must be fully in-office with the manager present five days a week, with no exceptions

That is simply how inside sales works; at Snowflake he found distributed inside sales reps and managers scattered across states reporting to a manager in Seattle, which was an inefficiency

26:34 Inside sales must be co located with the manager