Top Sales Management Challenges: First-hand Perspectives 

Disclaimer: The views and opinions expressed in this article are those of the individual contributors and do not reflect the official policy or position of their current or previous employers. This content is for informational purposes only.

Introduction

As I’ve highlighted in previous articles, including my recent piece on essential sales manager skills, the role of a sales manager is one of the most demanding in GTM.

It’s a very complex role that combines the need to oversee daily team operations with the responsibility of making strategic decisions – a balance that brings unique challenges and pressures. 

One of my contributors actually provided a very useful example overview of everything they have on their plate daily as a sales manager:

“…work on the vision / strategy / action plan and communicate about it; coach team members; challenge pipeline; help in customer meetings and in closing big opportunities; anticipate growth and potential blockers; resolve daily problems raised by the team; hire new people; provide a complete and detailed reporting; plus all the HR-related actions (vacations, expenses, bonuses…)” 

To understand just how challenging the role can be, I talked to a number of sales managers from around the globe about their biggest challenges.

I tried and (in my opinion, at least) succeeded in gaining insights from a varied enough group of contributors, spanning various markets (North America, Europe, and Asia) and representing companies from startups to large corporations with thousands of employees. 

As always, the contributors’ insights revealed a role even more complex than I had imagined, with nuanced perspectives on their responsibilities, teams, markets, and much more. 

I’m grateful to the 17 contributors who took time out of their busy schedules to share their experiences: 

Boris Piquet – Head of Sales

Daniele Protani – Sales Manager

Deividas Zilinskas – Sales Director, Global Cloud

Franck Richard – Country Sales Manager France

Galit Weinberg – Director, Sales Development & SMB Sales

Joseph Adrian Aranas – Head of Sales

Lee Gregory – Head of Sales

Lucas Le Boursicaud – Team Lead Business Development, UK&I

Matt Cope – Head of Sales UK&I

Marta Schiavone – Sales Manager Italy

Megan Wipff – Sales Development Manager

Parker Begale – Sales Development Manager

Rachael Raymond – Head of Broker Sales

Tyler Graham – Senior Sales Manager

Thomas Drost – Regional Sales Director Northern Europe

Veronika Elchishcheva – Sales & Business Development Manager

Vik Puri – Manager of Account Management

Naturally, the contributors didn’t participate just to “vent”; they also offered some valuable suggestions for tackling the management challenges they’ve encountered over their careers. 

For more ideas on how to tackle challenges as a sales manager, make sure to check out my article on sales management best practices.

Investigating the top sales management challenges

As you will discover, my contributors focused on a number of themes that are obviously at the top of their minds.

While the themes where the challenges appear may be shared by a number of sales managers I talked to, you will find many nuances in how their challenges manifest and how they tackle them.

These key themes include:

If you’re aspiring to become a sales manager, read on to get a sense of what awaits you.

If you’re already in the role, it’s reassuring to know that others are in the same boat as you.

For senior sales leaders, this is an opportunity to explore ways to support your managers in their development. 

And if you’re in sales enablement, rest assured that more than a few of the challenges shared by our 17 contributors are ones we, as enablers, can help address.

Managing teams and individual reps

While the role of a sales manager entails a huge number of responsibilities, the majority of their day is spent in the trenches with their team – putting out fires, offering advice, and navigating both group dynamics and individual performances.

It is therefore no surprise that many of my contributors mentioned these as some of their most prominent challenges.

For Veronika Elchishcheva, Sales and Business Development Manager at a gamification software company, arguments over markets and accounts present a considerable challenge. According to her, in a global company where all sales reps work in English, it’s not always clear who should cover which market:

“Some markets were easier to convert, others less so – and each sales rep wanted to excel and earn commission, hence the arguments over ownership.

The solution seems straightforward – define territories and allocate them fairly, establish a structure for periodic adjustments, work on a KPI structure, and incentivise collaboration.

But when the team is used to a toxic environment with poorly defined boundaries and competition, it is extremely difficult to make a change.”

Another day-to-day challenge that Veronika faces is managing underperformers. She even mentions how it is her biggest challenge because she finds it personally frustrating. She goes on to say:

“It is challenging firstly because you were the one who hired and onboarded the employee (if not, you trained and coached them over time), yet they still underperform. So the question is – whose fault is it?

It is also a very delicate task – to identify the reasons behind it and provide constructive feedback without completely demotivating the employee.

I create an improvement plan with workshops and meetings where we focus on weak areas, which usually helps to improve performance.”

Veronika wraps things up with the confession that the hardest task for her is letting go of underperformers who don’t improve over time.

On the topic of improving, allowing team members to learn from failure is important but challenging, as Boris Piquet shares:

“It’s difficult for most sales managers, even more when you got an internal promotion from IC to manager, to let people fail instead of telling them how to do things.”

Boris believes that sometimes you need to let team members try their way, even if you feel they’re not heading in the right direction:

“Instead of telling them what to do, you need to let them go, try their way, and fail… it’s very difficult but in the end, it brings so many learnings for everyone, and in the medium and long term, you all increase your skills.”

I love his punchy summary of these points:

“Let people try and fail.“

Matt Cope, Head of Sales at a company behind AI-powered accounting solutions for the hospitality industry, shared his challenges of managing remote sales teams. He pointed out three aspects of it that are made more difficult because the sales teams don’t share a physical office:

Performance management – “One key way to keep an eye on sales team performance is staying close to the numbers (inputs and conversion rates) but good performance is much more than numbers on a speadsheet.

To identify areas for improvement, you often need to sit in on calls/listen back retrospectively, which is less scalable than being able to overhear multiple conversations in an office environment and coach in realtime.

Conversation intelligence tools out there like Gong can help, but they are not a replacement for being there in the moment.”

Peer-to-peer learning – “A big part of how we learn is to hear or see something, mimic it, and then repeat. The same can be said for learning what not to do.

When you’re working remotely, this is much more challenging to do because you’re not able to overhear people’s sales conversations or see the ways in which they work as easily. This is especially a challenge for new salespeople who can miss out on a big part of their formative years in sales.”

Culture – “Being remote, you need to find new ways to maintain a great sales team culture and keep the morale high.

It’s great to try and get people together when possible, but face-to-face meetings are much less frequent, so it can be challenging to maintain personal relationships in the same way that you can in an office environment.”

Lucas Le Boursicaud, Team Lead Business Development for UK&I at a spend management platform, had some great advice for sales managers taking charge of a new team, based on the challenges he had experienced himself.

For one, he espoused the importance of a clear and shared vision:

“You need to be clear about your expectations and the verbatims you use and establish a common set of values. Indeed, even if a company already has values, a team has to make them its own in order to embrace them as much as possible and make them its own. 

As soon as they arrive, managers must communicate to let the sales team members feel that the work they do has a real impact and contributes to common and concrete objectives. 

However, the key is to make these objectives meaningful.” 

Lucas also mentioned the challenge that is innate to taking on a new team – identifying the strengths and the weaknesses of individual salespeople and how to best utilise them:

“The team is an orchestra.

Each team member is unique, and a sales manager needs to understand and build on the strengths and weaknesses of each team member. One of the major challenges here is to quickly identify them in order to distribute responsibilities in the best possible way.”

He added:

“In the early stages of taking charge of a junior team, we don’t even talk about delegating the project.

First you have to observe in order to coach and potentially delegate if needed.

The diversity of skills, backgrounds, and approaches is a real asset, so use them in order to give to everyone enough space to progress and become better salespersons.”

Tyler Graham, Senior Sales Manager at a company that develops construction management software, pointed out the challenge of finding that fine balance between being involved too much and too little:

“As a manager you want to make sure you continually add value to your team through ongoing education on topics like competitor info, changes in the competitive landscape, sales skill building, etc..

While all at the same time not coming across as a micromanager and using up too much of your team’s time sitting in meetings and not letting them sell.”

Parker Begale, Sales Development Manager at a spend management platform explains how important it is to scratch beyond the surface when you notice that a rep is underperforming before you start taking action:

“In order to coach sales reps well, understanding where their challenges and gaps exist is extremely important. However, these obstacles can disguise themselves as other issues that aren’t the root of the problem at its core.

I.e., you think the problem is the way a rep closes a call, but they actually aren’t prospecting/reaching out to the right type of prospect.

It takes some serious digging and brainpower to address the right roadblocks.”

Forecasting and quotas

Given that a sales manager’s performance is largely judged by their team’s quota attainment and the overall sales targets, it’s no wonder that quotas and forecasting are near the top of the mind when they discuss their biggest challenges.

For Marta Schiavone, Sales Manager for Italy at a company behind world-famous recruitment software, monthly sales quotas are easily in her top 3 sales management challenges:

“One of the biggest challenges I face as a sales manager is making sure every Full-Time Equivalent (FTE) salesperson hits 100% of their monthly quota.”

Marta also provided some suggestions on how sales managers can help with this:

“I make sure to follow up on deals every day so nothing slips through the cracks and the pipeline keeps moving.

I also get involved in important demos or follow-ups, especially for more complex deals, to help close key opportunities. Regular call reviews using tools like Jiminny are great for giving specific feedback, helping the team improve on things like handling objections or closing.

Setting short-term, achievable goals is a good way to help everyone stay on track.”

Thomas Drost, the Regional Sales Director for Northern Europe at a leading P2C platform broke down his quota-related challenge into a couple of pipeline-specific issues, while providing some advice on how to address them:

“Pipe Management – With purchases being the new scarcity, buying decisions involve more factors, more cycles, and more decisive planning.

My team executes on the deep discovery with all stakeholders to create and grind out a robust business case focused on value.

Pipe Conversion – The nature of present-day enterprise selling is painful. That pains us, because we are supposed to ease the buying journey of the buyers, yet keep an effective grip on timelines.

We also dedicate efforts towards knowing our “diamonds” that could realistically “close” within the quarter.

Giving these opps laser focus and going above and beyond tends to be more effective than keeping too much pipe open for too long and, in doing so, not being able to win the ones you could win.”

For Megan Wipff, Sales Development Manager at an account-based GTM data platform for B2B enterprises, the quota challenge is somewhat different and has to do with the fact that she often has to deal with SDRs and AEs having clashing priorities:

“AEs and SDRs have different priorities as reflected by their quotas, and as morale gets lower, pessimism gets higher.

AEs are more frugal with which opps they decide to invest time in, and SDRs feel the pain in their own attainment.”

While I expected forecasting to be one of the biggest challenges, I wasn’t expecting so many factors to be complicating the issue. 

For instance, for Daniele Protani, Sales Manager at the #1 job site in the world, among the many things, it has to do with the nature of the product:

“Accurate forecasting due to the recruting advertising platform we sell, therefore, no easy sometimes to predict the spend per client “

In the case of Vik Puri, Manager of Account Management at a company behind AI-powered cybersecurity and IT management software, the forecasting is complicated by the diversity of the EMEA market:

“The EMEA market is incredibly diverse, with each country presenting different economic conditions, buying behaviors, and regulatory environments.

This complexity makes accurate forecasting challenging.

Effective pipeline management here involves not only close monitoring but also educating leadership on regional realities to set realistic expectations.”

Marta Schiavone added inconsistency of data into the mix:

“Forecasting sales accurately is a big challenge. It’s essential because good forecasts help us make better decisions, allocate resources properly, and plan ahead.

Bad forecasts can lead to overestimating or underestimating revenue, which could result in poor decisions – like overhiring or underinvesting – and that can shake investor confidence.

The biggest problem here is inconsistent data input.

The sales team must be updating the CRM regularly and using solid qualification frameworks like BANT or MEDDIC.

This helps us get a clearer picture of where each deal stands. I also use historical data and predictive analytics in the CRM to fine-tune our forecasts, spotting patterns in sales cycles and win rates.

Breaking down the pipeline into stages and adding weighted probabilities gives us a more realistic view of deal progress instead of assuming every opportunity will close.”

Strategy, methodology and high-level processes

While many of the sales management challenges that contributors mentioned were related to day-to-day activities, which have a more pressing effects on their work, a number of them also acknowledged the importance of seeing things from a bird’s-eye view; in other words, more strategically. 

For Rachael Raymond, Head of Broker Sales in a major finance company, the ability to pivot quickly in response to external factors is vital. Operating in the lending space, she emphasises that they are:

“… at the mercy of a number of external factors, BoE base rate, prevalence of government schemes etc., so being able to pivot our offering and re-evaluate where we can extract value and opportunity is vital to succeeding at this level.

Without the ability to quickly execute changes (whether that be product, sales strategies, process or behavioural), we’d suffer far more when the market is volatile.“

Echoing the need for adaptability, Lee Gregory, the Head of Sales at a leading authority on all things MEDDIC, highlights the danger of a fixed mindset. He asserts:

“…individuals, teams, departments, entire companies need to have a growth mindset. Just because something worked yesterday doesn’t mean it will work today.”

He also warns that without instilling a culture of bravery and openness to change, businesses risk stagnation.

Boris Piquet, Head of Sales at a startup in the search API field with extensive managerial experience in a well-known fintech organisation, explicitly emphasises the necessity of taking a step back. He observes that “it’s easy to focus solely on immediate team performance, pipelines, deals, and handovers, but it’s crucial to take a step back from time to time.” 

He even gives advice on how to do this in-the-flow-of-work:

“QBRs or MEDDPICC reviews are great opportunities to reflect on what we’ve done, what are the plans on deals or for the next quarters… bringing people all together to think about specific topics.

If we’re 5 in a room, our total experience will be more impactful than the most experienced AE by himself.

Taking a step back and reflecting honestly is not easy, but it can change a B player into an A player.”

Implementing effective sales methodologies is another crucial strategic aspect, especially at times of major change. Deividas Zlinskas, Sales Director, Global Cloud at a major (3,500+ employees) company that delivers workforce management systems, is navigating the shift from selling into SMB and lower mid-market to targeting mid-market and enterprise clients.

He notes that adopting a new sales methodology is critical, but equally important is “sticking with inspection and coaching to ensure it does not fade off.” 

Process inefficiencies can significantly hinder sales performance and make the lives of sales managers even more difficult.

Galit Weinberg, Director of Sales Development & SMB Sales at a well-known fintech company that specialises in bank payments, points out that:

“…complex internal workflows, slow decision-making processes, and poor cross-departmental communication can significantly slow down the sales cycle and impede sales productivity.”

These bottlenecks lead to missed opportunities, longer closing times, and frustrated customers. 

She adds some very salient advice:

“Sales leaders need to focus on optimising these processes, often through automation, clear communication, and cross-functional collaboration, to ensure a smooth and efficient sales experience.”

Similarly, Joseph Adrian Aranas, Head of Sales at a company behind a leading document workflow platform, highlights the impact of process and system limitations on sales momentum.

He adds:

“We should be able to adapt to the dynamic nature of the market and buyers. It is critical for sales leaders to have a bi-annual review of tools that their workforce is using to address gaps and limitations on what you can ‘currently do’ and what you ‘cannot do’”. 

Morale and motivation

Motivating a sales team and keeping morale high is an integral part of a sales manager’s role.

In an environment where rejection is common and pressure to meet targets is intense, maintaining a positive and motivated team becomes both a challenge and a necessity.

My contributors shared their insights on the complexities of boosting morale and effective strategies to keep their teams engaged.

For Megan Wipff, low morale is a significant challenge, especially in outbound sales where rejection is frequent. She notes:

“As we face more rejection working outbound, morale dips, attainment suffers, and PIPs happen.” 

The constant stream of rejection not only affects individual performance but can also lead to performance improvement plans, making it crucial to find ways to keep spirits high and prevent a downward spiral in team morale.

Similarly, Deividas Zlinskas emphasises the importance of team morale during uncertain times and periods of change.

He highlights that maintaining a positive team spirit is essential when external factors create instability, as it directly impacts the team’s cohesion and productivity.

Motivating a culturally diverse team adds another layer of complexity.

Vik Puri shares his experience managing teams across the EMEA region:

“What drives a salesperson in Germany might differ greatly from what resonates with someone in the UK/I region or Southern Europe.

This requires tailoring motivational strategies to align with local values and work habits, while also balancing them with the expectations from US-based leadership, who may not always grasp these regional differences.” 

Echoing the need for a tailored approach, Marta Schiavone believes that “a one-size-fits-all approach doesn’t work” when it comes to keeping the team motivated.

She explains:

“Different things drive everyone, so you need to personalize your approach.

Some might be motivated by extra bonuses and prizes  – like rewarding the top performers for booking the most meetings or making the most cold calls.

For others, it’s more about recognition, so shouting them out on Slack or in team meetings can go a long way.”

As sales reps gain experience, traditional incentives may start to lose their impact.

Tyler Graham, highlights this challenge:

“As sales reps have been in role for 3+ years, the normal sales contests, spiffs, flash contests, etc., become non-motivating like they used to.

So trying to stay on top of new ways to incentivize and encourage your team to stay top of their game.” 

Creating an environment of trust and confidence is crucial for team morale according to Lucas Le Boursicaud who underscores this by referencing Ludovic Girodon‘s book “Dream Team”:

“Confidence is a key element in establishing genuine collaboration. One of the mistakes you can make is to think that you have to win your team’s trust. In fact, you don’t have to try to be liked but, moreover, you need to be respected by your team.”

He adds:

“This can be achieved by allowing the team to speak freely, by giving them the feeling of having a manager who fights for his team and his ideas. You need to create an environment where everyone can contribute without fear in order to smash quotas and targets.”

For Parker Begale, it is all about balancing positivity, realism, and accountability:

“You must focus on all 3 of these aspects of being a leader. But not too much of one or the other.

If you’re too positive, you become “toxic” or “overly” positive.

If you’re too realistic, you’re negative.

If you hold people accountable “too often” you’re a micro-manager.

You have to make sure you’re balancing these characteristics well at all times and playing the right cards at the right time.”

Cross-departmental collaboration

Sales teams don’t operate in isolation; their success is often intertwined with the efforts of other departments like marketing, product development, operations, and more.

Effective collaboration across these departments is very important for achieving common goals and ensuring a seamless experience for customers.

However, navigating these relationships can present significant challenges for sales managers.

For Rachael Raymond, collaborating and communicating effectively across internal teams is a major challenge, especially in rapidly growing companies.

She notes that when a business scales quickly, it doesn’t always scale its systems and processes accordingly.

This misalignment becomes most apparent in how internal stakeholders communicate and work with each other:

“I’ve seen this a number of times where a business has scaled quickly and seen great success, but with it, they haven’t also scaled their systems and processes which may no longer be fit for purpose at this larger scale.

This rears its head most prevalently in how internal stakeholders effectively communicate and work with each other. 

Often what is required is to completely re-evaluate chains of command, how problems are solved, how information is distributed, etc.

When done well, this ensures that you don’t have different people and departments doubling up on initiatives, projects are managed effectively, and ultimately we best equip our sales teams.”

Echoing the importance of alignment, Lee Gregory emphasizes that organisational alignment boils down to everyone understanding the Why.

“If engineering, product, marketing, sales, customer success, etc., are not aligned, everything is fragmented, and customers do not maximize value.”

For Daniele Protani, the misalignment between sales operations and the sales department is a pressing issue.

This lack of alignment can hinder the sales team’s ability to execute strategies effectively and meet their targets, highlighting the need for cohesive planning and communication between these functions.

Marta Schiavone discusses the complexities of managing relationships with various internal stakeholders like marketing, product, partnerships, support, customer success, and finance:

“Each department has its priorities, which don’t always line up with the sales team’s goals. So, building strong relationships and making sure everyone’s aligned is super important for success.”

She advocates for promoting a One Team mentality to break down silos and ensure that all departments work toward the same objectives:

“It’s about breaking down silos, aligning KPIs, holding cross-department meetings, and celebrating wins together. When everyone understands how their work contributes to the bigger picture, it helps everyone stay accountable and focused on growth.

Recognizing how each department helps drive revenue makes everyone feel invested in the outcome, strengthening communication and team spirit across the company.”

Joseph Adrian Aranas highlights the pain of misaligned goals and KPIs between sales and other departments, particularly marketing:

“The most difficult meetings are when sales and marketing teams don’t meet on the goal.

The key is for sales leaders to focus on the goal and not on the individual KPIs.

This is often a mistake when KPIs are not aligned with the goals.”

He suggests that setting the overarching goals or targets first allows for the establishment of individual KPIs that are aligned across all stakeholders:

“Set the goals or target first, and from there we can set individual KPIs to every stakeholder.”

While not strictly a cross-departmental issue, fluctuating priorities from upper sales leadership can significantly impact a sales manager’s ability to maintain alignment and focus within their team.

Tyler Graham shares his experience with this challenge:

“This one is an ongoing issue that I am sure plagues all sales managers.

Upper leadership has a meeting and decides there is a problem or something that needs fixing. They report on said issue, and it becomes top priority to fix immediately, and all focus must be on said topic.

They meet again 1-3 months later and identify a new problem (probably stems from over-focus on the previous problem), and now that is the issue that is all hands on deck.”

While not a matter strictly about interdepartmental collaboration, these shifts in focus from leadership act as external factors that can disrupt a sales manager’s plans and the team’s momentum. 

Talent-related challenges

Turnover rates are notoriously high in sales.

According to Harvard Business Review,  estimates of annual turnover among U.S. salespeople run as high as 27%—twice the rate in the overall labour force.

This constant churn makes hiring and retaining top talent one of the most pressing challenges for sales managers and organisations as a whole.

My contributors shared their experiences and insights on navigating these talent-related hurdles.

For Lee Gregory, talent acquisition, development, and retention are critical to achieving success:

“Without the right talent, you cannot achieve anything. When recruiting for talent, I’ve often looked for behaviors over and above experience and current sales skills.

So, once you bring on board the talent, how do you continually develop them to reach their potential?

If you don’t, they will leave and go to someone who will.”

Echoing the difficulty in hiring, Franck Richard, Country Sales Manager for France at a leading cloud provider in corporate compliance, investor relations, and ESG, emphasises the challenge of finding the right Account Executives at a reasonable price:

“It’s normal to pay a premium for talented salespeople, but they don’t understand that there’s an economic equation between their salary and the margin of the solution to be sold.

It’s very difficult to have a proper match.”

Matt Cope discusses the complexities of identifying top talent, especially in startup environments where the “right fit” is still being defined. He points out:

“It can be challenging to decide between hiring experienced reps and nurturing new talent, both in terms of cost, time, and risk.

Just because someone has performed well in another environment doesn’t necessarily mean they will perform well in your environment.”

He also highlights the risks associated with bad hires (which I also touched upon at the very beginning of my sales onboarding guide):

“Bad hires can cost a lot more than just their salaries and recruitment fees.

There’s a significant time investment in onboarding people, which could have been used elsewhere.

It can also have a negative knock-on impact on team culture if you consistently hire people who are the wrong fit and have to part ways.”

Parker Begale is a proponent of the hire slow-fire fast approach:

“Finding the right people for your sales team is challenging, especially remotely.

In today’s job market: many candidates apply to any potential fitting role. Often presenting well from experience.

So you have to take time with interviews and really focus on team fit, sales process alignment, and your leadership expectations. 

And ‘firing fast’ sounds harsh. It just means setting clear performance expectations from the start allows for quick decisions.

Sales is performance-based, and both the team and individual benefit when standards are upheld.”

The last two contributors who spoke about the challenge of hiring and retaining the best talent have somewhat specific points of view. 

For Vik Puri, this stems from the fact that he is hiring across the diverse EMEA region:

“Attracting and retaining top sales talent in EMEA is particularly challenging given the competitive nature of the market and the diverse cultural expectations.

Company culture, flexibility offered, and overall compensation packages have made is extremely tiresome to find the right talent.

Additionally, retention requires offering career growth and support tailored to the distinct professional aspirations and work-life balance priorities, which may not always align with the company’s global policies.”

Joseph Adrian Aranas talks about regions where businesses are outsourced or offshored, while highlighting the dangers of hiring the wrong profiles:

“It’s important that the right profiles are hired for the sales roles.

Often, a mistake is when we start filling up the positions with talents that have little to no exposure for key sales roles like sales managers, account executives, etc.

The key is to find the skill sets rather than working on a budget.

Top talent doesn’t come cheap, so we need to consider these things when setting up sales teams.”

Competition and lead generation

The issues of increased competition and more difficult lead generation are closely intertwined: as competition intensifies, capturing the attention of potential prospects becomes more demanding.

Additionally, the overload of outbound outreach has led to prospects becoming increasingly desensitised to traditional methods.

The contributors shared their experiences navigating this challenging environment.

For Megan Wipff, catching the attention of prospects has become harder than ever. She emphasises that:

“…creative and heavily researched messaging is a must at pretty much all stages of outreach.” 

Echoing this sentiment, Thomas Drost highlights the necessity of personalisation and relevancy in the face of growing competition and crowded outbound channels. He explains:

“With distress coming from more competitors and more crowded outbound spent spaces, personalization is a must.

We develop account-based strategies to be heard through those distractions.

Customers don’t want businesses to sell to them; they want businesses to know what they want from the beginning.”

Franck Richard sheds light on the difficulties of reaching prospects through traditional channels:

“Most people are used to email outreach and LinkedIn InMails; they don’t even read them anymore.

And with remote work, calling them by phone has become impossible unless you have their mobile phone number (very unlikely).

So I have to be creative with my team to reach our prospects by using other ways.”

Staying ahead of the competition is a constant battle for Rachael Raymond:

“It’s constantly equipping our sales teams to effectively sell against our competition and continuously upskilling them on this in order to maintain credibility with our customers.”

Similarly, Deividas Zlinskas points out the need to adapt when competitors catch up:

“Understanding when your competition caught up with your pitch and you need to adjust or change your decks and talk tracks.”

Technology and data

Sales organisations are leveraging more technology than ever before – from advanced CRM systems to AI-driven coaching tools, the tech stack available to sales professionals is vast and continually expanding.

While these technologies offer significant opportunities for efficiency and insight, they also present challenges. 

Managing and standardising data remains a critical issue, despite the plethora of tools designed to address it. My contributors shared their experiences navigating the complexities of technology and data in sales management.

For Boris Piquet, the multitude of tools available can be both a blessing and a curse. He observes:

“The tools are our friends.

Nowadays, tech companies buy a lot of tools to try to help the sales team as much as possible… and some are way more helpful than others.

As a manager, it’s important to keep super aware of the tools’ benefits and usage to help the team get the most out of them.”

He suggests organising sessions where sales reps share their experiences with different tools, discussing the benefits they find.

“When it’s collaboratively done, which is not easy and takes time, it’s priceless help.”

Galit Weinberg similarly highlights the dual nature of technological advancements:

“The fast-paced evolution of technology, particularly AI-driven tools and CRM systems, is both a challenge and an opportunity for sales managers. 

Staying on top of the latest technologies, integrating them into sales processes, and ensuring the team is well-trained can be a daunting task.

The challenge is finding the right balance between adopting new tools and not overwhelming the team with too many systems.”

Access to quality data is crucial for sales success, especially in outbound strategies. Matt Cope shares his challenges in arming sales reps with high-quality data:

“In certain markets, especially SMB, it can be particularly challenging to identify key prospects and acquire their contact details.

For outbound, arming salespeople with high volumes of high-quality contact data can make a significant difference in their overall performance.”

Matt points out that while data providers can assist, their coverage may be poor in some markets, especially when prospects have little online presence. “The alternative is lots of manual research, which is very time-consuming and takes sales reps away from what they should be doing – selling,” he notes.

Veronika Elchishcheva discusses the ongoing challenge of ensuring proper CRM hygiene and data entry:

“I think it’s a typical challenge for many team leads. While SDRs/BDRs are generally better at maintaining data hygiene, AEs/Sales are much more difficult to manage.

Data entry is crucial for analyzing which segment/industry/size targets perform and convert better, how long the sales cycle is, or how many touches we needed per lead to convert.”

She acknowledges that while this data is important for analysis, sales reps are primarily focused on booking meetings, closing deals, and reaching their KPIs:

“It is an ongoing challenge for me, despite having worked extensively on motivating both teams to keep data clean and optimizing to minimize manual data entry.”

Conclusion

Much like in my collaborative article on sales enablement challenges and sales leadership challenges, the collective insights shared by the contributors paint a vivid picture of the various challenges sales managers face on a daily basis.

Throughout strategic obstacles and the minutiae of daily team management, they lead their teams to sales success in an environment that feels more adversarial with each day that passes.

One of my personal favourite aspects of this article is that the contributors didn’t just express their biggest hurdles, but also came forward with high-quality, potential solutions for everyone to benefit from.

Thank you Boris, Daniele, Deividas, Franck, Galit, Joseph Adrian, Lee, Lucas, Matt, Marta, Megan, Parker, Rachael, Tyler, Thomas, Veronika, and Vik!

Make sure to check out my exploration of the sales leadership vs sales management discussion, as it perfectly complements these insights.