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How do you retain good talent, especially when sales roles are in such high demand across the industry?

Katie Harkins

Glide VP of Sales • 3y

Without sales, you don't have a business. Talented sales people are hard to find and even harder to retain. Here are a few questions I ask: Are your sales people bought i...

508 Views

As a hiring manager, what do the best sales candidates have in common?

Brian Tino

AlphaSense Senior Director, Strategic Sales • 3y

Good question! I evaluate every sales candidate who is interviewing to join my team on the same 3 criteria: 1. Sales Skills & Knowledge - key expertise & skills ...

2,331 Views

What communications framework do you use when communicating strategy 1) up to C Suite or 2) out to stakeholders?

Justin Offermann

ComfyUI Head of GTM • 4mo

Communicating strategy up to the C-suite: align on why now, what changes, and what the upside is. • Vision (zoomed out): what becomes possible if we get this right (growt...

717 Views

How are you leveraging AI for coaching, forecasting, and call reviews while maintaining data privacy and rep trust?

Katie Walsh

HubSpot Director of Sales • 5mo

I think about AI in sales leadership as an accelerant and the foundation has to be trust.We use AI to help reps and managers see patterns faster, coach more consistently,...

420 Views

What hiring profile and interview process yield top-performing AEs in your segment, and how do you reduce ramp time?

Katie Walsh

HubSpot Director of Sales • 5mo

The ones who have a high learning velocity, resilience, and customer curiosity.I hire for how people think, not just what they’ve sold. Top AEs show strong problem-solvin...

408 Views

What operating cadence (forecast calls, pipeline reviews, QBRs) drives accountability without creating meeting fatigue?

Katie Walsh

HubSpot Director of Sales • 5mo

One that’s purpose-built, not stacked. Every meeting should earn its place by changing decisions or behavior.I’m ruthless about meeting intent. Forecast calls exist to as...

448 Views

Which leading indicators best predict quarterly outcomes in your motion, and how do you socialize them with managers and reps?

Katie Harkins

Glide VP of Sales • 1mo

Operation goose egg. Get on the board early in the quarter. It's not just psychological, it changes the quality of selling for the rest of the quarter. When you're huntin...

155 Views

How do you enforce pipeline hygiene and consistent stage definitions without turning it into administrative overhead?

Katie Harkins

Glide VP of Sales • 1mo

Forecasting fiction destroys your credibility. Past close dates aren't forecasts, they're history. Dead deals don't hurt you. Undiscovered deal deals do. I see too many s...

155 Views

How do you manage a remote or hybrid sales force to maintain culture, collaboration, and consistent performance?

Katie Walsh

HubSpot Director of Sales • 5mo

Managing a remote or hybrid sales force really comes down to intentionality.I anchor everything in clarity.Clear expectations around goals, behaviors, and how work gets d...

914 Views

What is your framework for win/loss analysis, and how do you operationalize the insights across teams?

Katie Walsh

HubSpot Director of Sales • 5mo

Capture the reality, identify patterns, and turn insights into behavior change. If it doesn’t change how teams sell, it’s just reporting.First, I focus on getting clean, ...

487 Views

What is an important KPI that you see sales teams completely missing?

Yusuf Bulan

HubSpot Director Sales DACH • 1y

The sales equation is quite simple:Pipeline x Average Sales Price x Close Rate = RevenueIf not all KPIs are measured leading to this equation we are missing out. Focus sh...

1,042 Views

What are some sales kpis that are hard to track or less commonly tracked but that you think move the needle?

Katie Walsh

HubSpot Director of Sales • 8mo

Champion Engagement Score Track how often your internal champion initiates contact vs. you chasing them. Champions who go quiet = deals that die. Most CRMs can't measure ...

931 Views

What are good sales OKRs?

Tim Britt

Freshworks VP Partnerships • 2y

Sales OKRs should be designed to align with the overall business objectives and drive measurable outcomes that contribute to revenue growth and customer success. Here are...

702 Views

What role do Sales KPIs play in improving forecast accuracy, especially in unpredictable markets, and what approaches help teams make the most of these metrics?

Katie Walsh

HubSpot Director of Sales • 8mo

KPIs alone don't improve forecast accuracy - disciplined pipeline management does. Most teams are drowning in metrics but can't predict what's actually going to close nex...

998 Views

How well do typical KPIs around deal progression capture potential bottlenecks in the sales pipeline, and what are some effective strategies to accelerate the sales cycle across different customer segments?

Helen D'Abreo

SurveyMonkey Director, Expansion Sales • 1y

KPIs that are looking at the length of a sales cycle can identify bottlenecks in the pipeline and highlight opportunities that have been in the pipeline for too long. For...

1,133 Views

Setting KPIs can often feel arbitrary, especially when entering new markets. How do you get past this uncertainty to set realistic goals?

George Cerny

Collectly VP of Sales • 2y

"You can't improve what you don't measure" - Peter Drucker. When starting out in a new market, there can be lots of uncertainty. This uncertainty is the starting point,...

1,533 Views

What KPIs should I own and not own?

I'm working at a start-up, and a first sales hire.

Katie Harkins

Glide VP of Sales • 3y

If you have a quota, you should take ownership over all your KPIs. Make sure you make them easy to find in one dashboard. I usually call this my "Birds Eye View." I usual...

1,595 Views

How do you manage accountability for pipeline generation on a weekly basis, and what steps do you take when these expectations aren’t met.

Alicia Lewis

Rei Notionライフハック2万部突破！ Mid-Market Sales Leader • 10mo

Each week we keep pipeline generation expectations simple and visible. Managers set weekly targets and inspect them consistently. AEs are expected to keep roughly 4x cove...

627 Views

How do you structure, hire, and train a high performing sales culture

Alicia Lewis

Rei Notionライフハック2万部突破！ Mid-Market Sales Leader • 10mo

This is the approach that we take when structuring, hiring and training our sales group. Hire for talent density and values fit. At Notion, we set a high bar for judgment...

659 Views

What is the best way to create and roll out a repeatable and scalable renewal process when joining as a revenue leader?

Greg Baumann

Outreach Sr Director of Strategic and Enterprise Sales • 10mo

However early you think you need to be getting out in front of your renewal process? Double it. Early bird gets the worm -- work with the cross-functional teams to unde...

414 Views

What is your advice for creating and/or improving the sales process when joining a small but growing team? Particularly for a small company with no or little structure?

Alicia Lewis

Rei Notionライフハック2万部突破！ Mid-Market Sales Leader • 10mo

My advice would be to stand up the lightest workable process you can actually run, then iterate weekly. I've found great value in building the process with one or two res...

498 Views

How does sales leadership differ between a small and large company?

Tim Britt

Freshworks VP Partnerships • 2y

Sales leadership in a small company versus a large company involves navigating different challenges, priorities, and dynamics. Here are some key differences:Scope and Sca...

1,071 Views

What is the best way to align sales and customer success to increase positive outcomes for customers?

Michael Buscemi

Zip Sr. Director of Sales • 10mo

This is so hard. The best way to do so is to make sure your sales team understands what a good customer looks like. What a good customer looks like.What are the typical p...

503 Views

What's the earliest stage a startup should consider hiring a sales manager?

Michael Buscemi

Zip Sr. Director of Sales • 10mo

Assuming you are maturing from founder led growth, once the founder has more than 6 direct reports. AND, you think you don’t need founder involved in each deal.

1,084 Views

Question about org structures - what does your sales team org structure look like?

Nick Feeney

Loom VP, Revenue • 1y

With most of these questions, there isn't a one size fits all. Consider things like:Company stageGrowth objectivesGTM strategyCustomer segmentationSelf serve vs. sales le...

677 Views

What are the biggest surprises when going from a company where sales was established to one where you have to establish sales?

Andrew Zinger

Ironclad Senior Global Director, Revenue Enablement • 11mo

This is a great question and something a lot of leaders underestimate until they’ve lived it. Moving from an established sales org to being the person who has to establis...

430 Views

What's your framework to prioritizing needs/deliverables when you're the first sales leader at a company establishing the function?

Katie Harkins

Glide VP of Sales • 2y

#1 Need = REVENUE. Never forget that. Do everything in your power to exceed your number, everything comes after that. When you're the first sales leader at a company you'...

853 Views

How do you coordinate and work cross functionally with the demand generation team to create commonly shared KPIs?

Andrew Zinger

Ironclad Senior Global Director, Revenue Enablement • 11mo

When sales and demand gen work off different gtm plans, alignment breaks down fast. In my experience, the key is to co-create KPIs that are tied directly to revenue outco...

448 Views

What are the key processes you'd set up when expanding the sales team from 1 to multiple people?

Jessica Holmes

Adobe Director, Adobe Sales Academy • 1y

Moving from a solo sales person to a full team requires more than just adding headcount—it demands structure. I'd suggest the following when expanding your sales team fro...

574 Views

What does your sales team org structure look like?

Jeff Michaels

Mobivity Vice President, Sales & Marketing | Formerly Kibo Commerce, FedEx, ACCO, IPIX • 3y

While answering the "sales team org structure" is easy, it can quickly lead sales leaders and organizations down a constrained, unscalable path requiring frequent restruc...

3,281 Views

What advice would you give to someone tasked with taking the sales function up market in an existing business structure?

Jessica Holmes

Adobe Director, Adobe Sales Academy • 1y

Moving upmarket—selling to larger customers with more complex needs—is a major growth lever and very exciting! But, it’s also a shift that requires new thinking, new proc...

510 Views

If your sales team has only one or two people responsible for covering multiple products with complex features, how would you recommend dividing the workload in the short-term so as best to support long-term growth and expansion of the team?

Jessica Holmes

Adobe Director, Adobe Sales Academy • 1y

When your sales team is just one or two people, but your product suite is broad and technically complex, it’s easy to get stretched thin. The challenge is balancing short...

476 Views

Do you have any advice for a junior who is a first sales hire?

Jessica Holmes

Adobe Director, Adobe Sales Academy • 1y

Being the first sales hire at a startup is a unique opportunity—and a big responsibility! You’re not just selling the product; you’re helping build the sales function fro...

507 Views

When is a good time to start making big changes with sales processes? Our CEO believes we are too small 200+ employees to adopt a sales methodology. I have implemented best practices, rules of engagement, sales process, and all sales training. The only thing we lack is a methodology to bring the team together and unite us. We have made very large gains in ARR & ACV over 120%, but seem to have plateaued. I have approached my CEO many times always trying to improve culture, training, and support and find that it's the hardest part of my job to get him on board. I have proven myself with hard data and still can't seem to get through. The usual response I get is we just need to focus on getting X quarter sales in.

Adam Wainwright

HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 1y

Great question. This is a common challenge, especially in startups that often focus on immediate results.At 200+ employees, adopting a sales methodology is not just appro...

665 Views

How do you communicate sales updates and activities to the rest of the company?

Eric Martin

Vanta Head Of Sales • 2y

This is a great question, and how we have done this at Vanta has evolved over the years. Being thoughtful about how sales communicates updates to the rest of the company ...

1,604 Views

How does "the way you motivate" your sales org change as your company scale?

Brian Tino

AlphaSense Senior Director, Strategic Sales • 3y

Good question! When it comes to motivation, at any stage & maturity of a sales organization, you need to make sure: 1. Purpose - your sales team understands the miss...

2,658 Views

What's your best sales 30-60-90 day plan to make a big impact at a new company?

Greg Baumann

Outreach Sr Director of Strategic and Enterprise Sales • 1y

Great Question! In the 30-60-90 plans that I've created + seen done well, I've noticed a trend that:Month 1 is "identity", meaning becoming a value-add corporate citizen ...

1,261 Views

(How) do you include top performers on certain KPIs to set benchmarks you want people to work against?

Yusuf Bulan

HubSpot Director Sales DACH • 1y

Absolutely yes! We celebrate high performers in team meetings (also broader teams) and share their attainment and other KPIs (not all of course). We also share averages a...

1,128 Views

I've seen plenty of sellers regularly miss on their KPIs, but still reach or exceed quota, so why have more than 1 KPI (quota attainment)?

Brian Tino

AlphaSense Senior Director, Strategic Sales • 2y

Quota attainment & revenue will always the most important outcomes of any sales organization. However, the most mature sales organizations can align on a set of KPIs ...

1,250 Views

What are some of the worst KPIs to commit to achieving?

Richard Harris™

The Harris Consulting Group Founder • 3y

There are several kinds of KPIs. Some of the KPIs at the top of the funnel may not be worth much, however, the same type of KPI at the middle or bottom of the funnel may ...

1,095 Views

What are some KPIs that you find over-hyped and/or unimportant?

George Cerny

Collectly VP of Sales • 2y

By far the most over-hyped KPI is total pipeline created. This is certainly a key metric to track week over week as a health check, but it provides little insight into wh...

2,958 Views

What's your process for figuring out what metrics to hold sales accountable for?

George Cerny

Collectly VP of Sales • 2y

To effectively define the metrics for which you should hold sales accountable, I look at a few things:Understand the "Sales Math" of the business across some core univers...

2,757 Views

How do you recommend socializing KPIs (before the work starts and when it's done)?

Yusuf Bulan

HubSpot Director Sales DACH • 1y

I would recommend to share KPIs very early on. Transparency helps to set expectations and progress. It allows to celebrate success and also to identify areas for improvem...

656 Views

How do you develop quarterly/annual sales OKRs and tie those to individual projects?

Beau Noonan

Matterport Enterprise Sales Director • 3y

Here is my approach to aligning quarterly/annual sales OKRs with broader business objections:Define business objections: Identify the key regional business objectives for...

1,866 Views

What is your 30-60-90 day plan when you go into an org with the intention of setting up a sales function for the first time?

Nick Feeney

Loom VP, Revenue • 1y

This isn’t a one size fits all approach. Every leader should bring a different focus to their 30-60-90 day plan based on their leadership style, the stage in which the co...

2,157 Views

What's the most effective way to scale a sales team beyond the first few reps?

Roee Zelcer

TikTok Head of Sales, Products & Services • 3y

Essentially, scaling a successful sales team all comes down to the people you hire. The members you are adding as part of your team will define the team culture. I always...

4,665 Views

How do you think about shared KPI’s with your demand generation? And what are ones that sales teams often miss?

Adam Wainwright

HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 1y

When it comes to shared KPIs with demand generation, the approach can vary depending on the maturity of the company. Here’s how I think about it:Early-Stage Companies: Fo...

554 Views

How do you think about your first 30/60/90 day goals when coming in as the Head of sales in a startup that didn't have sales before?

Tim Britt

Freshworks VP Partnerships • 2y

When stepping into the role of Head of Sales at a startup that hasn't previously had a dedicated sales function, it's crucial to establish a strong foundation while drivi...

957 Views

How do sales KPIs change with a self-serve product?

Katie Harkins

Glide VP of Sales • 3y

Compared to a sales-assisted org, your KPIs change with a self-serve product. You want product lead growth that funnels your NRR to feed your MRR that feeds your ARR (Ann...

1,870 Views