"How are sales leaders thinking about territory design as remote work reshapes where buyers actually are?"

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Look, I'm dealing with a complete mess right now. We've got reps who moved to Austin, Miami, Denver during COVID and never came back, but they're still working accounts that were assigned based on where they lived in 2019. Meanwhile, I've got prospects in these markets getting covered by someone who's never set foot in their city. The real kicker? My comp plan still has geographic multipliers baked in - so I'm paying SF rates to a rep who moved to Nashville but kept their book. And don't get me started on the overlap issues - we've got three different reps claiming the same Fortune 500 account because their subsidiaries are scattered across time zones. I need to redesign this whole thing but I'm terrified of blowing up Q4 numbers while I figure it out.

What's the most important thing you need to understand or solve here?

Look, my number one priority is making sure my reps can actually reach their quotas, and right now territory design is completely screwed up because of remote work. I've got reps in Chicago trying to work accounts where the decision-makers moved to Austin or Denver during COVID and never came back. The old zip code-based territories made sense when everyone was in the office, but now I'm losing deals because my Boston rep can't get face time with a prospect who's working remotely from Vermont. Meanwhile, my comp plan is still tied to these outdated geographic boundaries, so I'm basically penalizing reps for something totally out of their control. I need to figure out how to realign territories based on where buyers actually are, not where their company headquarters used to be.

What does 'good' look like to you — and how far are you from that today?

Good looks like my reps hitting 110% of quota consistently, not this feast-or-famine bullshit we're dealing with now. When I've got reps in Austin crushing it while my Chicago team struggles with the same accounts, that's a territory design problem, not a skills problem. Right now we're maybe 60% there. The pandemic totally scrambled our playbook — we used to carve territories by zip codes and industry verticals, but now my best enterprise deals are coming from random geographies because everyone's remote. I need data that shows me where the actual decision-makers are sitting, not where their corporate headquarters used to be. The comp plan gets messy fast when territories don't make sense anymore. Can't have my team fighting over who owns a deal when the buyer moved from San Francisco to Denver mid-sales cycle.

What would change your perspective on this entirely?

If the math stopped working, honestly. Right now I can justify territory adjustments because I can show a clear ROI — we moved Sarah from the West Coast to cover remote prospects nationwide and her numbers went up 34% in six months. But if remote selling plateaus or buyer preferences shift back to in-person, suddenly I'm explaining to my CEO why we're paying SF salaries for reps who could be anywhere. The other thing would be if our competitors figure out how to poach talent by offering better remote territory packages. I'm already seeing job postings for "remote AE, national accounts, $180K base" and that's making my Chicago-based reps ask questions I don't want to answer.

What question are you not being asked that you wish someone would ask?

Look, everyone's obsessing over remote work like it's some revolutionary thing, but nobody's asking me about the real nightmare: how do I track my reps when they're bouncing between home offices in different states for tax reasons? I've got people who moved to Florida during COVID, kept their Chicago territory, but now they're "visiting" clients from Miami. My comp plan wasn't built for that shit. And here's the kicker - nobody's asking how this affects quota attainment visibility. When my rep was in Chicago, I could swing by their desk, see who they were calling, feel the energy. Now? I'm flying blind until the monthly numbers hit. I need tools that give me real-time pulse checks on deal velocity, not just activity dashboards that show me they logged into Salesforce.

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Look, I'm getting hammered by the board on our sales efficiency metrics, and honestly? Our territory model is completely broken. We've got reps in Manhattan trying to cover accounts that moved their operations to Austin during COVID and never came back. Meanwhile, our Southeast rep is sitting on this goldmine of relocated tech companies but doesn't have the enterprise experience to close them. The real kicker is we're still paying Manhattan real estate premiums for talent when half our target accounts aren't even there anymore. I'm looking at our Q3 numbers and it's obvious — territories carved out in 2019 make zero sense in 2024. But sales leadership keeps pushing back on any redesign because they're terrified of disrupting existing relationships.

What's the most important thing you need to understand or solve here?

Look, the fundamental issue is that our territory assignments are still based on 2019 thinking. We've got reps covering Manhattan because that's where the Fortune 500 headquarters are, but those decision-makers are now working from their houses in Westchester or Connecticut. Meanwhile, we're underserving emerging markets where executives actually moved to permanently. The board keeps asking why our pipeline conversion is down 15% year-over-year, and honestly? It's because we're optimizing for office buildings that are half-empty while completely missing where the real buying influence has shifted. We need to redesign territories around where decision-makers actually live and work now, not where their business cards say they're located.

What does 'good' look like to you — and how far are you from that today?

Good territory design means my field teams can actually reach the accounts that matter, not chase ghosts in markets where our buyers have scattered to home offices in suburbs. Right now we're still operating on pre-2020 maps while our enterprise clients have gone fully distributed — I've got reps burning budget on downtown hotel costs to meet prospects who moved to Connecticut two years ago. The gap is massive. We're probably 60% there on identifying where decision-makers actually are now, but our coverage model is stuck in 2019. My board keeps asking why our cost-per-acquisition spiked and it's because we're optimizing for the wrong geography entirely.

What would change your perspective on this entirely?

If the data showed that physical proximity actually still drives deal velocity, I'd have to completely rethink this. Right now we're assuming digital-first sales is the future, but what if enterprise buyers still close faster when there's face-to-face interaction? I've got board members asking tough questions about our geographic coverage gaps, and if the numbers prove that local presence still matters for complex B2B sales, we'd need to pivot our entire go-to-market strategy. The other thing would be if we found out our remote reps are actually *less* productive long-term - not just in revenue but in relationship quality and customer lifetime value.

What question are you not being asked that you wish someone would ask?

Nobody's asking about the psychological impact of remote territory design on our field teams. Everyone's obsessed with the geographic optimization algorithms and coverage models, but I'm dealing with reps who've had the same downtown Manhattan territory for eight years and now their biggest prospects are logging in from their Hamptons houses or relocated to Austin entirely. My team's identity was built around knowing every coffee shop near the Goldman Sachs building, and now they're staring at Zoom screens wondering if they even understand their buyers anymore. The board keeps pushing for headcount efficiency, but I'm watching veteran reps have existential crises about whether relationship selling even matters when everyone's a floating head on a laptop. That's the conversation we should be having.

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Look, I'm wrestling with whether our current territory model is even generating ROI anymore. We've got reps covering geographic territories that made sense five years ago, but now half our prospects are working remotely from completely different states. My VP of Sales keeps asking for more headcount, but I need to see the math on whether redesigning territories around where buyers actually *are* now versus where their office buildings sit would let us squeeze more productivity out of our existing team first. If we can get 15-20% more coverage efficiency without adding bodies, that's a six-figure savings right there. But nobody's giving me clean data on how remote work has actually shifted our buyer geography.

What's the most important thing you need to understand or solve here?

Look, I need to see the hard ROI on territory redesign versus just letting our sales team figure it out organically. Right now we've got reps scattered across the Midwest making quota, and I'm not convinced spending money on fancy territory mapping software is going to move the needle enough to justify the cost. Show me exactly how many more deals we'll close or how much travel expense we'll cut - real numbers, not some consultant's theoretical 15% improvement that never materializes.

What does 'good' look like to you — and how far are you from that today?

Good looks like our sales team hitting 95% of quota with territories that actually make geographic sense, not these Frankenstein districts we carved up in 2019. Right now we're at maybe 78% quota attainment and I've got reps driving 4 hours between accounts because half their territory moved to Austin or Nashville during COVID. The math is brutal — we're spending $47K more per rep annually just on travel and lodging compared to pre-pandemic, and that doesn't even count the opportunity cost of windshield time. I need territories redrawn based on where customers actually are now, not where our org chart says they should be. If I could get our average drive time down to 90 minutes between accounts and bump quota attainment to 90%, that's easily a $2.3M swing in my favor. That's real money, not some fluffy "collaboration improvement" metric.

What would change your perspective on this entirely?

Look, if someone showed me hard data that remote territories are generating 15-20% higher conversion rates with the same headcount, that changes everything. I don't care about the feel-good stories about work-life balance - show me the numbers. If a rep can cover Phoenix from Detroit and close more deals because they're not burning time on planes and rental cars, then we need to completely rethink our cost structure. But I need to see actual P&L impact, not surveys about rep satisfaction.

What question are you not being asked that you wish someone would ask?

Look, nobody's asking me the real question: what's this actually costing us in lost deals? Everyone wants to talk about optimization and efficiency, but I need to know hard numbers. Are we missing revenue because our territory lines don't match where our buyers moved during COVID? The other thing - and this drives me nuts - is no one's asking about the implementation cost. Sure, redesigning territories sounds great in theory, but what's it going to cost me to retrain reps, update CRM, and deal with all the internal politics when Chicago thinks they're losing accounts to Atlanta? I need someone to walk me through the total cost of ownership, not just sell me on the upside.

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Look, remote work completely screwed up how we think about customer success territories. I used to have clean geographic regions where my CSMs could do quarterly business reviews in person, build those champion relationships over coffee meetings, you know? Now half my enterprise accounts have their main users scattered across four time zones and their decision makers working from a cabin in Montana. The real headache is that our health scores are all built on engagement patterns that assume people are logging in from corporate networks during business hours. When someone's working from their kitchen table in a different state, those signals get wonky. I'm seeing accounts that look like they're churning based on our traditional metrics, but when I dig in, it's just that the usage pattern shifted because everyone's remote now. We're basically flying blind on territory assignment because "location" doesn't mean what it used to mean.

What's the most important thing you need to understand or solve here?

Look, I need to know where my customers actually *work* now, not just where their company headquarters are. I've got accounts that were assigned based on the CEO being in Austin, but half their decision-makers moved to Portland during COVID and never came back. When my CSMs are trying to build relationships and plan QBRs, geography still matters for that face-to-face stuff that prevents churn. I can't have my Denver rep flying to Texas every month when the real champions are now scattered across three time zones. The whole territory model assumes people stayed put, and that's just not reality anymore.

What does 'good' look like to you — and how far are you from that today?

Good is when my CSMs can focus on actual customer outcomes instead of playing whack-a-mole with territory issues. Right now I've got accounts bouncing between reps because someone moved from Austin to Portland, or worse - we've got enterprise deals sitting in limbo because nobody knows if the buyer relocated during COVID and which AE should own it. I want clean handoffs, zero account orphaning, and health scores that actually reflect relationship continuity. We're probably 60% there - our ops team built some decent workarounds, but it's still manual territory adjustments every quarter that eat up a full week of my time that should be spent on QBRs.

What would change your perspective on this entirely?

If we stopped pretending geography matters for customer success. Look, I've got accounts in Austin, Miami, and Portland all managed by the same CSM in Denver, and their health scores are consistently higher than my "local" Colorado accounts. The data doesn't lie - it's about relationship quality and product fit, not zip codes. What would really flip my thinking is if someone showed me that remote buyer behavior actually made territories *more* important, not less. Like if distributed teams meant you needed hyper-local market knowledge or something. But honestly, my biggest enterprise renewals last quarter came from companies where I've never met anyone face-to-face.

What question are you not being asked that you wish someone would ask?

The question nobody asks is "How do you actually measure if your CSMs are building relationships that stick when accounts get reassigned?" Like, we're all obsessed with health scores and NPS, but when someone's territory gets redrawn and their accounts move to a new rep, that's where you see if the relationship was real or just transactional. I've watched million-dollar accounts churn six months after a territory change because the new CSM inherited a green health score but zero actual trust. We track everything except relationship transferability, and it's killing us in this remote world where people change jobs every 18 months.