The Product Manager — Sales Team Disconnect: Areas of Friction and How to Mend These

Howdy, product managers. This post isn’t about defining the product manager role, its responsibilities or providing educational materials. Regardless of your level of experience, background and the specifics of your industry, you must know by now that product management is one of the hardest jobs to define in any organization, exactly because it’s so different in every company.¹After all, I bet all of us have read and re-read Ben Horowitz’ “Good Product Manager, Bad Product Manager” work which unsurprisingly is still the PMs’ Bible so many years after it was written: the quintessential principles to be followed are still the same.

The goal of this blog post is to dissect the ecosystem in which the product manager invariably finds herself to be the centerpiece, define the various forces that exert pressure on the PM, and outline the pains that keep PMs awake at night (I’m in no way claiming this is an exhaustive list; I rather hope you’ll share your own experiences in the comments below). More specifically, my plan is to dig in the various aspects of PMs’ interaction with sales managers and teams as the latter are not only an endless source of pain for PMs but more importantly, this relationship is the underlying reason for the failure of a lot of products in various types of organizations and markets.

You might ask why I’m so interested in the PM & sales team dynamics more than other stakeholders like the product engineers and support team that PM needs to collaborate with? After all, seamless collaboration with the dev team is a foremost prerequisite for shipping a product in the first place. Well, polls show that what’s eating PMs today is often related to their work with the sales team.

According to the 2017 Pragmatic Marketing Survey on Product Management and Marketing, some of the reasons why PMs can’t enjoy a good night sleep and hit their numbers, are:

• 46% of PMs worry about sales reps requesting customized sales tools on an account-by-account basis
• 35% of PMs must commit to adding features in order to close a deal
• 31% of PMs stress about the sales pipeline being below the revenue forecast
• 30% of PMs are apprehensive of salespeople consciously avoiding selling their products in favor of other products in the company portfolio²

Additionally, a prevailing number of respondents are of the opinion that they don’t spend nearly enough time talking to customers (an average rating of 3.48 out of 9)³. More customer-centric initiatives will make PM’s better at their job — so they say.

I’ve spent nearly a decade in the product marketing trenches, sharing a lot of responsibilities with PMs, as there’s a very thin line between the two roles, in a private organization that managed to grow from a robust startup to close to a 1,000-employee business before it got acquired by a public company. Today, I’m back to the joys and pains of the early start-up dynamics in SessionStack. Hence this blog post will be speaking of and comparing product management challenges in two different worlds — the dynamics in bigger, geographically dispersed teams and the challenges that startup PMs face.

The CEO of the Product?

Yep, some of you may argue this is not exactly the case⁴. After all, most often than not, PMs don’t really have the leverage and discretion to influence and order teams and stakeholders what to do. Still, on a much smaller case, and by employing a consultative approach rather than by issuing orders, PMs are responsible for all aspects of their product success. This includes all disciplines that are related to the product, and the respective stakeholders behind them: development and QA, UX and design, customer service, marketing and sales, partners. Oftentimes, product managers are budget owners too, meaning not only are they responsible for helping the product team ship the right product to their users (as Josh Elman has so brilliantly summarized in his post), they are also held accountable for the overall success of the product in terms of revenue.

What’s more, the personality traits and qualities a PM must possess closely mimic the ones displayed by CEOs and founders alike:

• Be able to anticipate — always be prepared and in control
• Be a visionary — never lose the big picture to pressing short-term issues
• Display empathy — be able to walk in other people’s shoes in order to achieve a win-win outcome for all stakeholders and teams
• Delegate, translate and facilitate — a product manager’s multidisciplinary knowledge and background enables her to communicate in whatever language is necessary to deliver information across teams

In a larger organization, Product Management becomes the link between the top-level goals set at the strategic level and securing results that reflect those goals. When startups are founded by a visionary who drives the direction and development of the product, the founder(s) have a Product Management function and don’t even know it⁵. That’s exactly how it works for us at SessionStack: we build a tool that helps you see your web app defects through your user’s eyes. In essence, the product has a vast array of use cases: from offering a way to get the full context around replicating an error (you get a recording of the user session along with the error message and JavaScript stack trace), to a customer support solution to troubleshoot client issues real-time, to a tool for UX and product experts to identify broken user experience. Obviously, at this early stage, focus and vision are of utmost importance for success. Diverting product management responsibilities from the co-founders to a new hire at this point runs the risk of diluting the team’s motivation and high-level goals.

As we can see, both in large organizations and startups alike, things for PMs can go wrong on so many different levels:

• Friction with the dev team as new product updates are late due to last minute bug fixing and limited resources
• Instead of solidifying the product, releases introduce breaking changes and regressions
• Upper management is concerned with the product quality, the lack of transparency in the division’s work and the overall product contribution to the bottom line
• The ineffective communication that plagues developer and support team’s collaboration has a direct impact on customer issue resolution and ultimately, customer success and stickiness
• There’s growing pressure from sales team that the poor product quality and customer support affect badly their ability to close deals and renew licenses
• Various customer requests keep on creeping in the roadmap
• Product UX: customer on-boarding rates are painfully low
• What is your biggest pain? Give us a shout in the comments

While product management is responsible for solving all these challenges, the reason why they exist in the first place does not always result from their actions (or lack of such thereof). Sometimes, the organization culture will not allow you to escape the bad PM omen. In her post “Warning signs that your new Product Management job is going to suck” Sue Raisty has managed to devise a funny but painfully accurate list of the symptoms of a plagued PM environment.

Unsurprisingly, stakeholder management is one of the most important aspects of the PM function: success would mean creating collaborative, mutually respectful personal relationships with each and every one who has a say about the PM’s work.

The archetypal sales rep: the PM’s biggest enemy. Or is she?

Of all the teams and stakeholders that Product Managers must work with regularly, sales teams are likely perching on top of the frustrating >> enjoyable experience ladder. Common PM complaints include things like “they have no clue about the product”, “they lie to leads and customers just to get their bonus”, “they just refuse to sell my product”, while on the other end one can hear things like “my PM is incompetent”, “the last release was such a crap”, “PMs don’t even understand our customers”.

Here’s an awesome representation of a sales rep’s brain as viewed by a PM (a piece of art by Sue Raisty, the original can be found on her blog here).

We thought it’d be only fair to make an attempt at putting together a PM’s brain map as viewed by a sales rep:

A dive into the PM — Sales dynamics: the environment

The complexity of the sales team and product management relationship is defined by a lot of variables so before trying to dissect the heart of your own personal and professional relations with your sales team and managers, there’s a bunch of questions that got to be answered:

1. Is your organization engineering/technology-driven or sales-driven?

Depending on the maturity of your industry, products, and company, the focus of your organization is likely to differ. Clearly, you are unlikely to experience a disbalance towards a sales-driven approach in an early startup where you are still building your MVP, whereas this might be the case in a mature market where there’s a head-to-head competition mostly focused on pricing and additional services.

2. Is your development methodology waterfall or agile?

Undoubtedly, the engineering processes adopted across the company and for developing your product specifically will impact your interaction with the sales force too. If you are employing the agile methodology, you are likely to need to create sales tools, train the sales team, and demo the product to customers way more often as the product release cycle will be much shorter, bringing new bits to market on a continuous basis.

3. How large and mature is your organization?

Just like Mark Suster explains it, sales in a startup is often evangelical — depending on the level of organization maturity, there might be an enormous sales machine in place, just a single sales professional or one of the co-founders might be in charge of devising the sales strategy and operational work (which is what Mark suggests as being the best strategy for the early startup stage). Mark also talks about the phase after moving out of the evangelical stage when you are in a desperate need of standardizing the sales process.

“There are a lot of new business leaders who get stuck in this middle ground where process and tools become more important as tacit knowledge is no longer the way to share know-how and expertise with the rest of the sales team in the organization”, argues Mark.

4. What’s your sales model?

Does your product require a complex, consultative type of sale? Is your product sales model high touch, low volume? Or are you counting on high-volume sales? The answers to these questions will determine to a great extent the interdependence between the product management and sales functions necessary for the success of a product. If you are interested to learn how to better define your sales model complexity, here’s a great article by David Skok on the sales complexity impact on the organization’s viability.

Being a startup, we at SessionStack follow Mark Suster’s advice on centralizing the sales decision-making power and operational activities in the hands of 1–2 people who’ve been part of the organization from the start. With demand and sales volumes increasing, however, our next step would be to standardize knowledge sharing and sales tool creation to be able to on-board new sales team members and meet growing volumes while still have the flexibility to facilitate the needs of larger customers.

5. What’s the size of your company’s product portfolio?

In other words, what’s your power to negotiate with sales team? If your product is not a primary focus one at the moment, or selling your product is not quite reflected in your sales comp plans, don’t be surprised if your product gets neglected by the sales force.

I bet you can come up with loads of other aspects that color the relations between PM and Sales. If you feel like, share these in the comments.

Areas of PM — Sales friction and how to overcome them

“Empathy should be embedded into the entire organization,” writes Belinda Parmar in the Harvard Business Review. “There is nothing soft about it. It is a hard skill that should be required from the board-room to the shop floor.”⁶

The ability to place yourself in other people’s shoes and show understanding each time you communicate with a stakeholder is considered a top skill that will help you see the big picture and drive success for yourself and the organization.

Empathy can also help you see the root cause of the friction in a Sales — PM relationship:

• Is it really sales team promising new features to customers?
• Is it PM lacking vision?
• Or is the problem on a much higher level?

Also, forget not that right from the start sales team and product management have diametrically opposite goals by definition: one of the strongest antagonisms between PMs and sales managers is that while the former need to translate top management’s vision and mission to their own product line, be forward-thinking and anticipate quarters, if not years ahead, the latter are very much short-term goal focused: how are we closing the month, the quarter, the year? Yes, sales reps don’t need to have vision, they have comp plans⁷. In essence, anything that complicates the sales cycle, slows it down, or shrinks the size of a deal is negative, while anything that helps them bag a purchase order or increase the average deal size is eagerly embraced.

Here’s a random and far from comprehensive list of typical areas causing frustration between sales team and product management, and how you can go about each one. And if you wonder how the heck did you manage to the get the toughest and always questioning sales reps for your product, don’t fret over it. Аll this is a sign your sales manager knows what she’s doing.

Friction areas:

1.Communication: even when there’s communication between PMs and sales, oftentimes it’s sporadic, and the two warring camps rarely speak the same language. Clearly, communication challenges vary depending on the above-mentioned environmental aspects like company size, product iteration velocity, sales model, etc.

How to mend the disconnect:

• Proactively engage with the sales team to get valuable feedback from customers
• Listen to your sales team for shifts in industry trends
• Accompany sales team on calls with existing customers and prospects
• Attend sales reviews to collect more info on the roadblocks they run into
• If you listen carefully, sales reps will help you identify ways to make your products shine in new markets
• Be crystal clear you are on sales team’s side, willing to help them: listening to their ideas, requests, and concerns can significantly improve the entire communication process.
• Help, don’t preach — sales team is the face of the company and they are on the front line. Assist them first, inspect and fix the process that got them to need urgent support later.⁸
• Keep it simple, be straight-to-the-point: if sales folks don’t see how the information you are presenting them is having a direct impact on their sales efforts, they will probably forget it.
• Be honest. Sales hate getting mislead about something the competition really does better. They’d look extremely unprofessional in front of customers and leads, which would ruin any credibility a rep might have for a consultative sale.
• Set up & announce clear communication channels that are not aimed at stifling collaboration but rather help speed up the feedback loops. Provide multiple channels for contributing product and competitive feedback such as dedicated e-mailboxes, Slack channels, intranets. Make it easy for the sales team to share what they know.
• Have salespeople attend product reviews: focus on your sales champions who have exhibited interest in helping you grow your product turnover.
• Team up sales and product managers at conferences and company expos.

2. Sales enablement: another common grey zone that causes complaints and despair. Sales team feel they never get the necessary training and tools from PM while the latter believes her efforts to train and educate the sales force are futile and time-wasting. Some thoughts on how to fix this:

• Don’t count on one-off trainings of your sales team (especially if you operate in an agile environment, where your product gets often updated). Organize continuous type of training for them; sales enablement is an important part of the product manager’s responsibilities and a way for her to show she genuinely cares about sales success.
• Don’t rely on sales team to proactively pull the materials from a central repository. Use a notification service to update them when new materials are posted.
• Come up with different formats for sales enablement: off-sites, lunch and learns, demos, surveys, videos, etc. Different people learn differently.
• Most companies have a standard sales deck. As sales teams grow and become distributed these sales decks transform over time. Make sure these get updated often enough to reflect changes in product, positioning, and strategy.
• Call scripts — put together a rough draft of these to navigate your sales force on what to talk about, who in the organization to call, and how to handle objections.

3. Objectivity: identify issues that might not be directly related to your responsibilities (such as post-sales support, technical support, product shipping logistics, legal, etc.) yet might be directly affecting the leads’ impressions and purchasing intent. Sit down with your sales team and nail it together: what are the negative responses and complaints they usually get?

4. Product releases are always a time of stress for the PM as there are so many things that can go wrong, and so many stakeholders to make happy. Good PMs always strive to deliver a smooth, well-orchestrated and timely product updates. Great PMs go the extra mile to always have a plan B, in case things go wrong, and sales reps appreciate contingency plans as it’s their comp plans and revenue targets at stake.

We at SessionStack can’t afford to have any downtime for example, as our customers access and monitor their sessions and problems through our web solution. Since SessionStack is monitoring 100% of clients’ web app user sessions (and any errors that might pop up during these sessions), any disruption in the monitoring of clients’ web applications would mean the latter will not be able to accurately and reliably replicate the errors end-users ran into or the number of users impacted by the issues.

5. The product roadmap:

‘If your company is a software company, it should NEVER build custom code for a particular deal. Yet many companies do this because they lack maturity and discipline.’ — Steve Johnson, Pragmatic Marketing

Adding/removing features from the roadmap has been a constant motive for tension between sales and PM. As is the case, nothing’s purely black or white, and different times (read, different organizational environment) call for different measures. Still, there are good practices that can be followed:

• Build your product to facilitate some level of extensibility and customization. There are generally three areas where customizations occur: UI/UX, workflow, and integration with third-party tools. Supporting these three types of customizations without breaking your product allows you to accommodate customers and prospects between release feature requests.
• Sit down with your sales manager and try to find out if she’s uncovered a genuine roadmap priority. Analyze, interview and survey.
• Sometimes the problem is that sales reps do not have the industry knowledge depth required to understand what the lead needs to solve a problem vs. what the prospect says she needs. In this case, you’d better get in touch with the prospect to understand her pain points.
• You’ve absolutely got to define what salespeople can and can’t say about your current and future products.⁹ Selling more than 3–4 months ahead of the curve will surely backfire for two reasons:

— Inevitably, some of the features will not end up in the product, and customers will be disappointed.

— Customers will keep their money in their pockets and will wait for the new product.

• Make sure you own the release of new product information to customers but let sales play the messenger role. SMs know which customers are likely to want a sneak peak of new functionality as Beta testers. They also know who might be evaluating the competition and need to be reassured. Simply, it’s in the best interest of product and sales management to collaborate to seed information on new releases to strategic customers.¹⁰

6. Understand the sales cycle: if you are to understand and empathize with sales team, you’ve got to have a very good understanding of how their lives run in the organization. Again, expect to find large differences in these models depending on the environmental aspects that we discussed above. In a consultative sale, it boils down to acquiring a prospect, finding a champion in her organization to guide you through the sales process, identify everybody involved in the decision and what their roles are, the budget owner most importantly, figure out who the competition is for this deal, demonstrate your unique value proposition relative to the competition and understand the buyer’s timeframe and decision process.¹¹

7. It’s you who should be performing a win/loss analysis, its purpose is to understand what happened in the sales cycle and how to increase the chances of winning the next deal. If you’re expecting to have your sales team do trend analysis across deals, or to deliver clear and concise summaries of their win/loss reports, you’re likely to be greatly disappointed.¹²

8. Product demos:

• Demos are instrumental in closing deals. Yet one of the things that most people are bad at and that are hard to standardize across the organization is the demo. “A good demo tells a story. A good demo walks the user through “a day in the life” of a user trying to do her job. 80% of demos I see are features, functions & benefits. People don’t buy features & functions. They buy solutions to their problems. So, you really need to script the storytelling of your demos to talk in your customer’s language. You need to train your staff to pause and ask questions & solicit feedback during the demo. In short, you need to institutionalize your company’s demos.”, says Mark Suster in his brilliant “Give your teams Swiss Army knives” article.
• Don’t oversell — if, while demoing, a prospect expresses her enthusiasm and interest in the product, it might be a good idea to leave it there. Describing additional features that the lead might not be currently interested in, can only distract her from reaching the conclusion she needs the product now.

9. Unite over ‘destroying’ the competition: by gamifying the quest to shipping a better than the competing product, and to acquiring a larger than competitors’ market share, PM and sales team can find a way to bury the hatchet.

10. Align measurements: product managers are usually evaluated based on a total revenue goal for their product. Salespeople often have a total revenue goal, which, for larger companies, can be spread across several products. Ensure you are on the same page with your sales team, and devise a common plan that outlines how these goals will be reached:

• Focused sales effort on product releases
• Pricing and SKU adjustments needed to succeed
• Combined effort and strategy at industry conferences and events

Most of you are certainly aware of these common situations of frustration and despair; if you have your own list, step forward and share them in the comments section.

A few inspirational stories in closing

Far from hoping to uncover new universal truths about how to achieve PM — sales equilibrium, this post’s aim was to get you thinking once again of the importance of product management — salesforce collaboration for the success of a product. We are all in the same boat, are we not?

Finally, I wanted to share a few interviews with product managers of iconic products that Marty Cagan has gathered and published in his article Behind Every Product. Learn about how:

• Jane Manning managed to bring Google AdWords to success despite the initial strong resistance from the sales team
• Lea Hickman achieved exceptional results for Adobe’s Creative Cloud and managed to alleviate sales team’s concerns of transitioning from larger reseller channels to directly dealing with customers

And a few more. Enjoy!

Finally, if you are ready to improve the overall product quality and customer support to make management and sales happy, you can get started with SessionStack for free here. SessionStack will:

• Help your dev team reproduce product defects faster and reliably thanks to errors replay, this way freeing up resources to be re-allocated to new feature development.
• Customers get ever more demanding to receive omni-channel live help and have their problems quickly resolved. With SessionStack, support team will be spending less time bugging developers and more time leveraging SessionStack to help users real-time.
• Understand whether your product is meeting the functional and usability expectations of the customers

References:

¹A Product Manager’s Job: https://medium.com/@joshelman/a-product-managers-job-63c09a43d0ec

²The 2017 Annual Product Management and Marketing Survey, Pragmatic Marketing, page 9: http://mediafiles.pragmaticmarketing.com/pdf/PragmaticMarkketingSurvey2017.pdf

³The 2017 Product Management Insights, Alpha: http://insights.alphahq.com/product-management-insights-2017

⁴Is The Product Manager CEO of the Product, Pragmatic Marketing: https://pragmaticmarketing.com/resources/articles/is-the-product-manager-ceo-of-the-product

⁵Pragmatic Marketing: Creating Product Management at a Startup: https://www.pragmaticmarketing.com/resources/articles/Creating-Product-Management-at-a-Startup

⁶Why empathy the most important business skill, Sharon Fischer: https://www.laserfiche.com/simplicity/why-empathy-is-the-most-important-business-skill/

⁷,¹² Ten Things Product Managers Should Know About Sales, Pragmatic Marketing: https://pragmaticmarketing.com/resources/articles/Ten-Things-Product-Managers-Should-Know-About-Sales

⁸Nine Things Product Managers Should Know About Supporting Sales, Pragmatic Marketing: https://pragmaticmarketing.com/resources/articles/nine-things-product-managers-should-know-about-supporting-sales

5 Questions Product Managers Should Ask Their Sales Teams, Maddy Kirsch, ProductPlan: https://www.productplan.com/questions-product-managers-ask-sales-teams/

⁹,¹⁰Sales v. Product Management: Why Can’t We All Just Get Along, 10 Miles Square: https://tenmilesquare.com/sales-v-product-management-why-cant-we-all-just-get-along/

¹¹Give Your Teams Swiss Army Knives, Mark Suster, Both Sides: https://bothsidesofthetable.com/give-your-teams-swiss-army-knives-c94980d86b68

How Product Managers Can Work Effectively with Sales, UserVoice: https://community.uservoice.com/blog/how-to-work-effectively-with-sales/

PM 101 — Working with Sales, The Clever PM: http://www.cleverpm.com/2016/05/25/pm-101-working-with-sales/

How To Be a Good PM: http://www.goodproductmanager.com/2008/03/06/work-effectively-with-sales/